N-(Heterocyclicaminocarbonyl)arylsulfonamides

ABSTRACT

N-(heterocyclicaminocarbonyl)arylsulfonamides, such as 3-isocyanato-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide or methyl [3-[[(4- methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]phenyl]carbamate, are useful for the regulation of plant growth and as herbicides.

RELATED APPLICATIONS

This application is a continuation-in-part of my copending applicationSer. No. 142,436, filed Apr. 21, 1980, now abandoned, which is adivisional of application Ser. No. 955,504, filed Oct. 27, 1978, nowU.S. Pat. No. 4,225,337, which is a continuation-in-part of applicationSer. No. 937,552, filed Sept. 1, 1978, now abandoned, which is acontinuation-in-part of application Ser. No. 840,168, filed Oct. 6,1977, now abandoned.

BACKGROUND

This invention relates to novelN-(heterocyclicaminocarbonyl)arylsulfonamides wherein the aryl groupthereof is substituted by an amino, isocyanato, carbamate, amido,thiocarbamate or ureido group. The compounds of this invention areuseful as agricultural chemicals, such as plant growth regulants andherbicides.

Netherlands Pat. No. 121,788, published Sept. 15, 1966, discloses thepreparation of compounds of the following formula and their use asgeneral or selective herbicides: ##STR1## wherein R₁ and R₂ mayindependently be alkyl of 1-4 carbon atoms; and

R₃ and R₄ may independently be hydrogen, chlorine or alkyl of 1-4 carbonatoms.

U.S. Pat. No. 3,637,366 discloses compounds having the formula: ##STR2##wherein R₁ is hydrogen or lower saturated aliphatic acyl; and

R₂ is hydrogen, 2-pyrimidinyl, pyridyl, amidino, acetyl or carbamoyl.

The disclosed compounds are said to provide control of crabgrass, cress,endive, clover and Poa annua.

French Pat. No. 1,468,747 discloses the following para-substitutedphenylsulfonamides as being useful as antidiabetic agents: ##STR3##wherein R=halogen, CF₃ or alkyl.

Compounds of the following formula, and their use as antidiabeticagents, are reported in J. Drug Res. 6. 123 (1974): ##STR4## wherein Ris pyridyl.

Logemann et al., Chem. Ab., 53, 18052 g (1959), disclose a number ofsulfonamides, including uracil derivatives and those having the formula:##STR5## wherein R is butyl, phenyl or ##STR6## and R₁ is hydrogen ormethyl. When tested for hypoglycemic effect in rats (oral doses of 25mg/100 g), the compounds in which R is butyl and phenyl were mostpotent. The others were of low potency or inactive.

Argentine Pat. No. 174,510 (attached hereto) teaches compounds of thegeneral formula: ##STR7## In this formula R¹, R² and R³ are equal ordifferent and represent hydrogen or alkyl or alkenyl groups which canalso be substituted for example by --OH, --Cl, --SH, --NO₂ or --NH₂groups. The radicals R¹ and R² can also be closed in the form of a five-or six-membered ring. R⁴ represents hydrogen or an alkyl or aryl radicalwhich can also be substituted. Between the group X and the radical R⁴there can also be an SO₂ group. X represents a bridge of oxygen,nitrogen or sulfur, which connects the CO group with a radical R⁴. Y isan atom of chlorine or the radical --CH₃, --CH₂ Cl, --CHCl₂ or CCl₃.

Wojciechowski, J. Acta. Polon. 19, p. 121-5 (1962) [Chem. Ab., 59 1633e] describes the synthesis ofN-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide:##STR8## Based upon similarity to a known compound, the author predictedhypoglycemic activity for the foregoing compound.

Substituted pyrimidinyl sulfonylureas of the following formula, whichare also para-substituted on the phenyl ring, are disclosed in FarmcoEd. Sci., 12, 586 (1957) [Chem. Ab., 53, 18052 g (1959)]: ##STR9## whereR=H or CH₃.

The presence of undesired vegetation causes substantial damage to usefulcrops, especially agricultural products that satisfy man's basic foodand fiber needs, such as cotton, rice, corn, wheat, and the like. Thecurrent population explosion and concomitant world food and fibershortage demand improvements in producing these crops. Preventing orminimizing loss of a portion of such valuable crops by killing, orinhibiting the growth of undesired vegetation is one way of improvingthis efficiency.

A wide variety of materials useful for killing or inhibiting(controlling) the growth of undesired vegetation are available; suchmaterials are commonly referred to as herbicides. However, the needstill exists for effective herbicides that destroy or control weedswhile not significantly damaging useful crops. Some weeds (nutsedge is aparticular example) are very difficult to control; many of theherbicides that are used to control nutsedge are so nonselective thatthey cause damage to the crops themselves.

SUMMARY OF THE INVENTION

This invention relates to compounds of Formula I and theiragriculturally suitable salts, suitable agricultural compositionscontaining them, and method of using them as pre-emergence and/orpost-emergence herbicides. ##STR10## wherein R₁ is H, Cl, Br, F, alkylof 1-4 carbon atoms, OCH₃, NO₂ or R₁₁ S(O)_(m) ;

R₂ is --NCO, --NHCOOR₃, --NHCOSR₃, --NHCOR₃, --NHCONR₄ R₅ or --NR₆ R₇ ;

R₃ is alkyl of 1-4 carbon atoms;

R₄ is H or CH₃ ;

R₅ is H, alkyl of 1-4 carbon atoms or methoxy;

R₆ is H or alkyl of 1-3 carbon atoms;

R₇ is H or alkyl of 1-3 carbon atoms; or

R₆ and R₇ taken together are

    --(CH.sub.2).sub.n -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --;

n is 4 or 5;

R₁₁ is alkyl of 1-3 carbon atoms;

m is 0 or 2;

X is methyl, methoxy or ethoxy;

Y is methyl or methoxy; and

Z is CH or N;

provided that:

(a) when R₂ is ortho to the sulfonylureido group, then R₁ must behydrogen and R₂ cannot --NCO;

(b) when R₅ is methoxy, R₄ is methyl;

(c) when R₂ is --NCO, the compound cannot be a salt; and

(d) when R₂ is --NCO, --NHCOOR₃ or --NHCONR₄ R₅ and Z is nitrogen, thenR₁ must be alkyl of 2-4 carbon atoms or R₁₁ S(O)_(m).

Preferred for their high herbicidal activity and/or favorable ease ofsynthesis are those compounds of Formula I wherein:

R₂ is --NR₆ R₇, --NCO, --NHCOOCH₃, --NHCOCH₃ or --NHCON(CH₃)₂ ; and

R₆ and R₇ are independently hydrogen or alkyl of 1-3 carbon atoms.

Also preferred for their high herbicidal activity and/or favorable easeof synthesis are those compounds of Formula I wherein:

R₁ is alkyl of 2-3 carbon atoms or R₁₁ S(O)_(m).

More preferred for their higher herbicidal activity and/or morefavorable ease of synthesis are those of the preferred compounds ofFormula I wherein:

R₂ is --NR₆ R₇ or --NCO;

R₆ and R₇ are independently hydrogen or methyl; and

X is methyl or methoxy.

Most preferred for their outstanding herbicidal activity and/or mostfavorable ease of synthesis are those of the more preferred compounds ofFormula I wherein:

R₁ is hydrogen, chlorine, methyl or methoxy.

Specifically preferred for the same reasons are the following compounds:

Methyl[3-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]phenyl]carbamate;

(1-Methylethyl)[3-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]phenyl]carbamate;

3-isocyanato-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide;

3-(3,3-dimethylureido)-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide;

2-amino-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide;

2-amino-N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide;

5-amino-N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-methylbenzenesulfonamide;

5-amino-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-methylbenzenesulfonamide;

5-amino-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methylbenzenesulfonamide;

5-amino-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-methylbenzenesulfonamide;

5-amino-N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-methylbenzenesulfonamide;

2-Methyl-5-[(methylamino)carbonylamino]-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide;

2-Methyl-5-[(methylamino)carbonylamino]-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide;

2-Amino-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide;

2-Amino-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide;

N-[2-[[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]phenyl]acetamide;

N-2[-[[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]phenyl]acetamide;and

N-[2-[[(4,6-Dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]phenyl]acetamide.

Synthesis

As shown in Equation 1, the compounds of Formula I wherein R₂ isisocyanato can be prepared by combining an appropriate 2-aminopyrimidineor 2-amino-1,3,5-triazine of Formula III with an appropriatelysubstituted m-isocyanatobenzenesulfonamide of Formula II; R₁, X, Y and Zbeing as previously defined. ##STR11##

The reaction is best carried out in inert aprotic organic solvents suchas methylene chloride, tetrahydrofuran or acetonitrile, at ambientpressure and temperature. The aminoheterocycle (III) is added slowly toa solution of the m-isocyanatobenzenesulfonyl isocyanate with stirring.Such slow addition favors reaction of the amine with the highly activesulfonyl isocyanate moiety of compound (II) rather than the arylisocyanate moiety thereof.

The reaction is generally exothermic. In some cases, the desired productis insoluble in the warm reaction medium and crystallizes from it inpure form. Products soluble in the reaction medium are isolated byevaporation of the solvent, trituration of the solid residue withsolvents such as 1-chlorobutane, ethyl ether or pentane, and filtration.

The intermediate m-isocyanatobenzenesulfonyl isocyanates of Formula IIcan be prepared from the correspondingm-amino-N-(butylcarbamoyl)benzenesulfonamides by reaction with phosgeneaccording to H. Ulrich, B. Tucker and A. A. R. Sayigh, J. Org. Chem. 31,2658-2661 (1966).

The isocyanato substituent in compound (I-A) can be converted readily tothe carbamates (I-B), thiolcarbamates (I-C), or urea derivatives (I-D)of this invention by reaction thereof respectively with the appropriatealcohol (Equation 2), thiol (Equation 3) or amine (Equation 4).##STR12##

The reactions of Equation 2, 3 or 4 can be carried out in situ withisocyanato compound (I-A), or isocyanato compound (I-A) can first beisolated and added to the alcohol, thiol, or amine neat or in anon-reactive solvent. In any event, the reactions of Equations 2, 3 and4 proceed readily and are mildly exothermic; however, in some cases, theaddition of a catalyst such as dibutyl tin dilaurate or 1,4-diazabicyclooctane may be used.

As shown in Equation 5, the compounds of Formula I wherein R₂ is aminocan be prepared by the catalytic hydrogenation of appropriatelysubstituted N-(pyrimidinylaminocarbonyl)nitrobenzenesulfonamide orN-(triazinylaminocarbonyl)nitrobenzenesulfonamide (which are disclosedin my previously filed applications Ser. Nos. 824,805, filed Aug. 15,1977 and 840,389 filed Oct. 10, 1977, the contents of which areincorporated herein by reference): ##STR13## The reaction of Equation 5is best carried out in polar solvents such as acetic acid or ethanol inthe presence of 5 to 10% palladium on carbon at ambient temperatureunder hydrogen pressure of 1 to 5 atmospheres. The amino compounds thusprepared can be acylated by acyl halides of the appropriate carboxylicacids according to Equation 6. ##STR14## These acylations are bestcarried out in a polar aprotic solvent such as methylene chloride oracetonitrile in the presence of an acid acceptor such as pyridine,collidine or triethylamine. Frequently the best results are obtained bycombining the acylating agent and acid acceptor in the anhydrous solventprior to the addition of the benzenesulfonamide.

In other cases, acylation of the aminobenzenesulfonamides as describedin Equation 7 is best carried out by using the appropriate anhydride asa solvent for the reaction or adding a two-fold excess of theappropriate anhydride to a warm concentrated solution of a suitableaminobenzenesulfonamide in a solvent such as chloroform or methylenechloride and refluxing from one to 24 hours. ##STR15## In some cases,the desired product is insoluble in the warm reaction medium andcrystallizes from it in pure form. Products soluble in the reactionmedium are isolated by evaporation of the solvent, excess anhydride andthe corresponding acid, trituration of the residue with solvent such as1-chlorobutane, ethyl ether or pentane, and filtration.

Alternatively acetylated derivatives can be prepared with the reactionof a suitable aminobenzenesulfonamide with ketene as described inEquation 7A. ##STR16## The reaction of Equation 7A is carried out bysuspending the aminobenzenesulfonamide in a solvent such asmethylenechloride, chloroform or tetrahydrofuran, treating thesuspension with an excess of ketene gas at ambient temperature andallowing the mixture to stand for one to three hours. The product isisolated by removing the solvent by evaporation and triturating theresidue with water to hydrolyze the by-products and cause the product tosolidify.

Ureido-substituted compounds can be prepared by reaction of theappropriate amine with a dialkylcarbamoyl chloride in the presence of anacid acceptor, such as pyridine, (Equation 8) or an alkyl isocyanate(Equation 9) neat or in aprotic solvent such as toluene, chloroform, ormethylene chloride. ##STR17##

Generally, N-alkyl- or N,N-dialkylaminobenzenesulfonamides can beprepared as shown in Equation 10 by reacting the appropriateaminobenzenesulfonamide in acetonitrile with an aqueous or acetonitrilesolution of a suitable aldehyde and sodium cyanoborohydride at roomtemperature and ambient pressure in a modification of the proceduretaught by R. F. Borch and A. I. Hassid, J. Org. Chem., 37, 1673 (1972).##STR18##

Alkylation of secondary aminobenzenesulfonamides can be effected using a3-10 fold excess of the appropriate aldehyde in the presence of sodiumcyanoborohydride. After the addition of the aldehyde, glacial aceticacid is added intermittently to adjust the pH to neutrality. Followingadditional stirring and dilution with water, the pH is again adjusted toneutrality and the desired products are isolated by extraction with asuitable solvent, such as chloroform, methylene chloride or ether,followed by evaporation of solvent and trituration of the residue withsolvents such as 1-chlorobutane, ethyl ether or pentane, and filtration.

Compounds wherein a dialkylamino, morpholino or pyrrolidino group ismeta to the sulfonyl can be prepared by the reaction of an appropriatelysubstituted benzenesulfonylisocyanate with the appropriate2-aminopyrimidine or 2-amino-1,3,5-triazine according to Equation 11.##STR19## The reaction is best carried out in inert aprotic organicsolvents such as methylene chloride, tetrahydrofuran or acetonitrile, atambient pressure and temperature. The aminoheterocycle (III-B) issuspended in the solvent and the sulfonyl isocyanate (II-B) is added tothe suspension. A mildly exothermic reaction generally occurs whichresults in a warm reaction mixture from which many of the desiredcompounds (I-B) crystallize in pure form.

As shown in Equation 12, the carbamates I-B and I-C, as well as thosecompounds of Formula I wherein the carbamate or thiocarbamate group islocated ortho to the sulfonyl group, can be prepared by reacting theappropriate amino-precursor therefor with an appropriate chloroformateester under the conditions described for the reactions of Equations 8and 9. ##STR20## wherein E is O or S.

The sulfonated intermediates required for the reaction of Equation 11can be prepared by way of chlorosulfonation, using methods reported inthe literature [cf. Holleman, Rec. Trav. Chim., 24, 31 (1905)]. When R₁is nitro, displacement of chlorine by reacting an appropriate secondaryamine with 5-chloro-2-nitrobenzenesulfonamide in a suitable solvent suchas ethanol will afford the required starting material for thepreparation of II-B. ##STR21## The preparation of5-chloro-2-nitrobenzenesulfonamide is described by J. G. Topliss et al.,J. Med. Chem. 6, 122 (1963).

Other sulfonyl chlorides, useful as intermediates for the preparation ofcompounds of this invention, are prepared by diazotization of theappropriate aniline with sodium nitrite in HCl, followed by the reactionof the diazonium salt with sulfur dioxide and cuprous chloride in aceticacid according to the teaching of H. L. Yale and F. Sowinski, J. Org.Chem. 25, 1824 (1960). The preparation of sulfonamides from sulfonylchlorides and ammonium hydroxide is widely reported in the literature,e.g., Crossley et al., J. Am. Chem. Soc. 60, 2223 (1938).

The intermediate sulfonyl isocyanates of Formulae II and IIb can beprepared by reacting corresponding sulfonamides with phosgene in thepresence of n-butyl isocyanate at reflux in a solvent such aschlorobenzene, according to the procedure of H. Ulrich and A. A. Y.Sayigh, "Newer Methods of Preparative Organic Chemistry", Vol. VI p.223-241, Academic Press, New York and London, W. Foerst Ed. In caseswhere formation of the desired sulfonyl isocyanate is difficult by theabove procedure the sulfonylurea formed by reaction of butyl isocyanatewith the appropriate sulfonamide is treated with phosgene according tothe above reference.

When R₁ is R₁₁ S(O)_(m) sulfonated intermediates can be prepared viachlorosulfonation [F. Holleman, above] of the appropriate alkylnitrobenzene sulfide. The sulfonyl chloride thus obtained is convertedto the sulfonamide and sulfonyl isocyanate as previously discussed.Oxidation of the o-alkylthiobenzenesulfonamide intermediates to sulfones(R₁ =R₁₁ SO₂) can be carried out in acetic acid with 30% hydrogenperoxide according to methods cited by C. M. Suter in "Organic Chemistryof Sulfur", John Wiley and Sons, Inc., New York, N.Y. 1944.

As shown in Equation 13 below, the acid addition salts of 2- or5-aminocarbonylbenzenesulfonamides can be prepared by heating at 40°-50°a suspension of the appropriate aminobenzenesulfonamide in a solventsuch as ethanol containing an equivalent amount of an acid such as HCl,HBr, H₂ SO₄, p-toluenesulfonic acid or trichloroacetic acid. In the caseof volatile mineral acids such as HCl or organic acids such astrichloroacetic acid an excess may be employed. Removal of solvent invacuo yields the desired ammonium salt. ##STR22##

The alkali metal salts of substituted benzenesulfonamides can beprepared as shown in Equation 14. The alkali metal salts can be obtainedby addition of one equivalent of the appropriate base such as metalalkoxide, hydroxide, or carbonate in a solvent such as methanol orethanol to a suspension of the appropriate benzenesulfonamide, in thesame solvent, followed by heating at 40°-50° and removal of solventunder reduced pressure. Residues are usually glasses which may betriturated with solvents such as ethylacetate, ethylether or hexane togive the desired solid alkali metal salts. ##STR23##

The ammonium salts of substituted benzenesulfonamides can be prepared asdescribed in Equation 15. Generally one equivalent of an appropriateamine such as ammonia, dimethylamine, diethanolamine or triethanolamineis added neat or in a solvent such as methylene chloride or methanol toa suspension of the appropriate benzenesulfonamide in the same solvent.The solvent is removed under reduced pressure to yield as product, thedesired ammonium salt.

In the following equation, equation 15, R₈, R₉, and R₁₀ areindependently selected from C₁ -C₁₅ alkyl, CH₂ CH₂ OH and phenyl.##STR24##

The synthesis of aminoheterocyclic derivatives has been reviewed in "TheChemistry of Heterocyclic Compounds", a series published by IntersciencePubl., New York and London. 2-Aminopyrimidines are described by D. J.Brown in "The Pyrimidines", Vol. XVI of the above series published in1962. 2-Amino-1,3,5-triazines are synthesized according to methods citedby E. M. Smolin and L. Rapaport in "s-Triazines and Derivatives", Vol.XIII of this series, published 1959.

The preparation of compounds of this invention is further illustrated bythe following specific examples wherein temperatures are in degrees C.

EXAMPLE 13-Isocyanato-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide

To 21 g of m-isocyanatobenzenesulfonyl isocyanate in 250 ml of anhydrousacetonitrile was added in small portions at ambient temperature, 14 g of2-amino-4-methoxy-6-methyl-1,3,5-triazine, and the mixture was stirredat ambient temperature for sixteen hours. The white precipitate thusobtained was removed by filtration and dried in vacuo. The resultantproduct, m.p. 260° dec, which is3-isocyanato-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide,showed an infrared absorption peak at 2210 cm⁻¹, consistent for thedesired compound containing one isocyanate function.

By using the procedure of Example 1 with an equivalent amount of anappropriate 2-aminopyrimidine or 2-amino-1,3,5-triazine and anappropriately substituted m-isocyanatobenzenesulfonyl isocyanate, thecompounds of Table I can be prepared.

                  TABLE I                                                         ______________________________________                                         ##STR25##                                                                    R.sub.1       R.sub.2  X        Y      Z                                      ______________________________________                                        H             NCO      CH.sub.3 CH.sub.3                                                                             CH                                     H             NCO      CH.sub.3 OCH.sub.3                                                                            CH                                     H             NCO      OCH.sub.3                                                                              OCH.sub.3                                                                            CH                                     H             NCO      CH.sub.3 CH.sub.3                                                                             N                                      H             NCO      OCH.sub.3                                                                              OCH.sub.3                                                                            N                                      Cl            NCO      OCH.sub.3                                                                              OCH.sub.3                                                                            CH                                     Cl            NCO      OCH.sub.3                                                                              CH.sub.3                                                                             CH                                     Cl            NCO      OCH.sub.3                                                                              OCH.sub.3                                                                            N                                      Cl            NCO      OCH.sub.3                                                                              CH.sub.3                                                                             N                                      Br            NCO      OCH.sub.3                                                                              CH.sub.3                                                                             CH                                     Br            NCO      OCH.sub.3                                                                              OCH.sub.3                                                                            CH                                     Br            NCO      OCH.sub.3                                                                              OCH.sub.3                                                                            N                                      CH.sub.3      NCO      OCH.sub.3                                                                              CH.sub.3                                                                             CH                                     CH.sub.3      NCO      OCH.sub.3                                                                              OCH.sub.3                                                                            CH                                     CH.sub.3      NCO      OCH.sub.3                                                                              OCH.sub.3                                                                            N                                      F             NCO      OCH.sub.3                                                                              CH.sub.3                                                                             CH                                     F             NCO      OCH.sub.3                                                                              OCH.sub.3                                                                            CH                                     F             NCO      OCH.sub.3                                                                              OCH.sub.3                                                                            N                                      OCH.sub.3     NCO      OCH.sub.3                                                                              CH.sub.3                                                                             CH                                     OCH.sub.3     NCO      OCH.sub.3                                                                              OCH.sub.3                                                                            CH                                     OCH.sub.3     NCO      OCH.sub.3                                                                              OCH.sub.3                                                                            N                                      NO.sub.2      NCO      OCH.sub.3                                                                              CH.sub.3                                                                             N                                      NO.sub.2      NCO      OCH.sub.3                                                                              OCH.sub.3                                                                            CH                                     NO.sub.2      NCO      OCH.sub.3                                                                              CH.sub.3                                                                             CH                                     CH.sub.2 CH.sub.3                                                                           NCO      CH.sub.3 CH.sub.3                                                                             CH                                     CH.sub.2 CH.sub.3                                                                           NCO      CH.sub.3 OCH.sub.3                                                                            CH                                     CH.sub.2 CH.sub.2 CH.sub.3                                                                  NCO      CH.sub.3 OCH.sub.3                                                                            CH                                     CH(CH.sub.3).sub.2                                                                          NCO      CH.sub.3 OCH.sub.3                                                                            CH                                     SCH.sub.3     NCO      CH.sub.3 OCH.sub.3                                                                            CH                                     SCH.sub.2 CH.sub.3                                                                          NCO      CH.sub.3 OCH.sub.3                                                                            CH                                     SCH(CH.sub.3).sub.2                                                                         NCO      CH.sub.3 OCH.sub.3                                                                            CH                                     SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         NCO      CH.sub.3 OCH.sub.3                                                                            CH                                     SO.sub.2 CH(CH.sub.3).sub.2                                                                 NCO      CH.sub.3 OCH.sub.3                                                                            CH                                     SO.sub.2 CH.sub.2 CH.sub.3                                                                  NCO      CH.sub.3 OCH.sub.3                                                                            CH                                     SO.sub.2 CH.sub.3                                                                           NCO      CH.sub.3 OCH.sub.3                                                                            CH                                     SO.sub.2 CH.sub.3                                                                           NCO      OCH.sub.3                                                                              OCH.sub.3                                                                            N                                      SO.sub.2 CH.sub.3                                                                           NCO      OCH.sub.3                                                                              CH.sub.3                                                                             N                                      SO.sub. 2 CH.sub.2 CH.sub.3                                                                 NCO      OCH.sub.3                                                                              CH.sub.3                                                                             N                                      SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         NCO      OCH.sub.3                                                                              CH.sub.3                                                                             N                                      ______________________________________                                    

EXAMPLE 2 Methyl[3-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]phenyl]carbamate

To an anhydrous solution containing 2.1 g of m-isocyanatobenzenesulfonylisocyanate and 30 ml of acetonitrile was added in small portions atambient temperature, 1.4 g of 2-amino-4-methoxy-6-methylpyrimidine withstirring. The mixture was stirred for sixteen hours at ambienttemperature, followed by the addition of 1 g of anhydrous methanol.Evaporation of the solvent yielded a gelatinous product which solidifiedwhen triturated with ethyl ether. The desired product thus obtaineddecomposed at above 120°.

EXAMPLE 3 (1-Methylethyl)[3-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]phenyl]carbamate

To an anhydrous solution of 2.3 g of m-isocyanatobenzenesulfonylisocyanate in 50 ml of methylene chloride was added in small portions1.4 g of 2-amino-4-methoxy-6-methylpyrimidine. Efficient stirring wasmaintained during the addition and for three additional hours. Theintermediate thus obtained,3-isocyanato-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide,was reacted further by adding one gram of 2-propanol and stirring theresultant mixture for an additional sixteen hours. Filtration of thereaction mixture and evaporation of the filtrate yielded the desiredproduct melting at 173°-180°.

By using the procedure of Example 2 or 3 with equivalent amounts of anappropriate 2-aminopyrimidine or 2-amino-1,3,5-triazine, an appropriatem-isocyanatobenzenesulfonyl isocyanate, and an appropriate alcohol orthiol, the compounds of Table II can be prepared.

                  TABLE II                                                        ______________________________________                                         ##STR26##                                                                    R.sub.1    R.sub.2      X       Y      Z                                      ______________________________________                                        H          NHCO.sub.2 CH.sub.3                                                                        OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                     H          NHCO.sub.2 CH.sub.3                                                                        OCH.sub.3                                                                             CH.sub.3                                                                             N                                      H          NHCO.sub.2 CH.sub.3                                                                        OCH.sub.3                                                                             OCH.sub.3                                                                            N                                      Cl         NHCO.sub.2 CH.sub.3                                                                        OCH.sub.3                                                                             CH.sub.3                                                                             N                                      Cl         NHCO.sub.2 CH.sub.3                                                                        OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                     Cl         NHCO.sub.2 CH.sub.3                                                                        OCH.sub.3                                                                             CH.sub.3                                                                             CH                                     Cl         NHCO.sub.2 CH.sub.3                                                                        OCH.sub.3                                                                             OCH.sub.3                                                                            N                                      CH.sub.3   NHCO.sub.2 CH.sub.3                                                                        OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                     CH.sub.3   NHCO.sub.2 CH.sub.3                                                                        OC.sub.2 H.sub.5                                                                      CH.sub.3                                                                             CH                                     CH.sub.3   NHCO.sub.2 CH.sub.3                                                                        OCH.sub.3                                                                             OCH.sub.3                                                                            N                                      Br         NHCO.sub.2 CH.sub.3                                                                        OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                     Br         NHCO.sub.2 CH.sub.3                                                                        OCH.sub.3                                                                             CH.sub.3                                                                             CH                                     Br         NHCO.sub.2 CH.sub.3                                                                        OC.sub.2 H.sub.5                                                                      OCH.sub.3                                                                            N                                      F          NHCO.sub.2 CH.sub.3                                                                        OC.sub.2 H.sub.5                                                                      OCH.sub.3                                                                            CH                                     F          NHCO.sub.2 CH.sub.3                                                                        OCH.sub.3                                                                             CH.sub.3                                                                             CH                                     F          NHCO.sub.2 CH.sub.3                                                                        OCH.sub.3                                                                             CH.sub.3                                                                             N                                      OCH.sub.3  NHCO.sub.2 CH.sub.3                                                                        OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                     OCH.sub.3  NHCO.sub.2 CH.sub.3                                                                        OC.sub.2 H.sub.5                                                                      CH.sub.3                                                                             CH                                     OCH.sub.3  NHCO.sub.2 CH.sub.3                                                                        OCH.sub.3                                                                             OCH.sub.3                                                                            N                                      H          NHCO.sub.2 C.sub.2 H.sub.5                                                                 OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                     H          NHCO.sub.2 C.sub.2 H.sub.5                                                                 OCH.sub.3                                                                             CH.sub.3                                                                             N                                      NO.sub.2   NHCO.sub.2 CH.sub.3                                                                        OCH.sub.3                                                                             CH.sub.3                                                                             N                                      NO.sub.2   NHCO.sub.2 CH.sub.3                                                                        OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                     NO.sub.2   NHCO.sub.2 CH.sub.3                                                                        OCH.sub.3                                                                             CH.sub.3                                                                             CH                                     H          NHCO.sub.2 C.sub.2 H.sub.5                                                                 OCH.sub.3                                                                             OCH.sub.3                                                                            N                                      Cl         NHCO.sub.2 C.sub.2 H.sub.5                                                                 OCH.sub.3                                                                             CH.sub.3                                                                             CH                                     CH.sub.3   NHCO.sub.2 C.sub.2 H.sub.5                                                                 OCH.sub.3                                                                             CH.sub.3                                                                             CH                                     Br         NHCO.sub.2 C.sub.2 H.sub.5                                                                 OCH.sub.3                                                                             CH.sub.3                                                                             CH                                     F          NHCO.sub.2 C.sub.2 H.sub. 5                                                                OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                     OCH.sub.3  NHCO.sub.2 C.sub.2 H.sub.5                                                                 OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                                 ##STR27##   OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                     CH.sub.3                                                                                  ##STR28##   OCH.sub.3                                                                             CH.sub.3                                                                             CH                                     Cl                                                                                        ##STR29##   OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                     F                                                                                         ##STR30##   OCH.sub.3                                                                             OCH.sub.3                                                                            N                                      Br                                                                                        ##STR31##   OCH.sub.3                                                                             CH.sub.3                                                                             N                                      OCH.sub.3                                                                                 ##STR32##   OCH.sub.3                                                                             OCH.sub.3                                                                            N                                      H                                                                                         ##STR33##   OCH.sub.3                                                                             OCH.sub.3                                                                            N                                      CH.sub.3                                                                                  ##STR34##   OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                     Cl                                                                                        ##STR35##   OCH.sub.3                                                                             CH.sub.3                                                                             CH                                     OCH.sub.3                                                                                 ##STR36##   OCH.sub.3                                                                             OCH.sub.3                                                                            N                                      H                                                                                         ##STR37##   OCH.sub.3                                                                             OCH.sub.3                                                                            N                                      H                                                                                         ##STR38##   OC.sub.2 H.sub.5                                                                      OCH.sub.3                                                                            CH                                     Cl         NHCO.sub.2 i-C.sub.3 H.sub.7                                                               OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                     F          NHCO.sub.2 i-C.sub.3 H.sub.7                                                               OCH.sub.3                                                                             OCH.sub.3                                                                            N                                      CH.sub.3   NHCO.sub.2 i-C.sub.3 H.sub.7                                                               OCH.sub.3                                                                             CH.sub.3                                                                             N                                      OCH.sub.3  NHCO.sub.2 i-C.sub.3 H.sub.7                                                               CH.sub.3                                                                              CH.sub.3                                                                             CH                                     H          NHCO.sub.2 n-C.sub.3 H.sub.7                                                               OC.sub.2 H.sub.5                                                                      CH.sub.3                                                                             CH                                     Cl         NHCO.sub.2 n-C.sub.3 H.sub.7                                                               OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                     F          NHCO.sub.2 n-C.sub.3 H.sub.7                                                               OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                     Br         NHCO.sub.2 n-C.sub.3 H.sub.7                                                               OCH.sub.3                                                                             CH.sub.3                                                                             CH                                     OCH.sub.3  NHCO.sub.2 n-C.sub.3 H.sub.7                                                               OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                     CH.sub.2 CH.sub.3                                                                        NHCO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                              OCH.sub.3                                                                            CH                                     CH.sub.2 CH.sub.2 CH.sub.3                                                               NHCO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                              OCH.sub.3                                                                            CH                                     CH(CH.sub.3).sub.2                                                                       NHCO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                              OCH.sub.3                                                                            CH                                     CH.sub.2 CH.sub.3                                                                        NHCO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                              OCH.sub.3                                                                            N                                      CH.sub.2 CH.sub.2 CH.sub.3                                                               NHCO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                              OCH.sub.3                                                                            N                                      CH(CH.sub.3).sub.2                                                                       NHCO.sub.2 CH.sub.3                                                                        CH.sub. 3                                                                             OCH.sub.3                                                                            N                                      CH(CH.sub.3).sub.2                                                                       NHCO.sub.2 CH.sub.3                                                                        OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                     SCH.sub.3  NHCO.sub.2 CH.sub.3                                                                        OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                     SCH.sub.2 CH.sub.3                                                                       NHCO.sub.2 CH.sub.3                                                                        OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                     SCH.sub.2 CH.sub.2 CH.sub.3                                                              NHCO.sub.2 CH.sub.3                                                                        OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                     SCH(CH.sub.3).sub.2                                                                      NHCO.sub.2 CH.sub.3                                                                        OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                     SCH.sub.3  NHCO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                              OCH.sub.3                                                                            N                                      SCH.sub.2 CH.sub.3                                                                       NHCO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                              OCH.sub.3                                                                            N                                      SCH.sub.2 CH.sub.2 CH.sub.3                                                              NHCO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                              OCH.sub.3                                                                            N                                      SCH(CH.sub.3).sub.2                                                                      NHCO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                              OCH.sub.3                                                                            N                                      SO.sub.2 CH.sub.3                                                                        NHCO.sub.2 CH.sub.3                                                                        OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                     SO.sub.2 CH.sub.2 CH.sub.3                                                               NHCO.sub.2 CH.sub.3                                                                        OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                     SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                      NHCO.sub.2 CH.sub.3                                                                        OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                     SO.sub.2 CH.sub.3                                                                        NHCO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                              OCH.sub.3                                                                            N                                      SO.sub.2 CH.sub.2 CH.sub.3                                                               NHCO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                              OCH.sub.3                                                                            N                                      SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                      NHCO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                              OCH.sub.3                                                                            N                                      SO.sub.2 CH(CH.sub.3).sub.2                                                              NHCO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                              OCH.sub.3                                                                            N                                      ______________________________________                                    

EXAMPLE 43-(3,3-Dimethylureido)-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide

A solution of3-isocyanato-N-[(4-methoxy-6-methylpyrimidin-4-yl)aminocarbonyl]benzenesulfonamidewas prepared as in Example 3 and to this was added 0.5 ml of liquifiedanhydrous dimethyl amine with stirring. The resultant mixture wasstirred for an additional sixteen hours and evaporated in vacuo todryness. Trituration of the residue with ethyl ether and filtrationyielded the desired solid product. The product was dissolved in water bythe addition of 50% sodium hydroxide to pH 13, filtered, and thefiltrate adjusted to pH 3 to cause precipitation of the desired product,m.p. 147°-157°.

EXAMPLE 53-(3-tert-Butylureido)-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide

To a solution of3-isocyanato-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamideprepared as in Example 3 was added 0.8 g of tert-butylamine at ambienttemperature with stirring. After sixteen hours, filtration of thereaction mixture and evaporation of the filtrate yielded the desiredproduct which after trituration with ethyl ether and isolation byfiltration melted at 137°-145°.

By using the procedure of Example 4 or 5 with equivalent amounts of anappropriate 2-aminopyrimidine or 2-amino-1,3,5-triazine; an appropriatem-isocyanatobenzenesulfonyl isocyanate, and an appropriate alkyl amine,the compounds of Table III can be prepared.

                                      TABLE III                                   __________________________________________________________________________     ##STR39##                                                                    R.sub.1  R.sub.2   X   Y   Z  m.p.                                            __________________________________________________________________________              ##STR40##                                                                              OCH.sub.3                                                                         OCH.sub.3                                                                         CH                                                 Cl                                                                                      ##STR41##                                                                              OCH.sub.3                                                                         OCH.sub.3                                                                         CH                                                 CH.sub.3                                                                                ##STR42##                                                                              OCH.sub.3                                                                         CH.sub.3                                                                          CH 155-157° C.                              F                                                                                       ##STR43##                                                                              OCH.sub.3                                                                         OCH.sub.3                                                                         N                                                  OCH.sub.3                                                                               ##STR44##                                                                              OCH.sub.3                                                                         OCH.sub.3                                                                         N                                                  H                                                                                       ##STR45##                                                                              OCH.sub.3                                                                         CH.sub.3                                                                          N                                                  Cl                                                                                      ##STR46##                                                                              OCH.sub.3                                                                         OCH.sub.3                                                                         N                                                  Cl                                                                                      ##STR47##                                                                              OCH.sub.3                                                                         CH.sub.3                                                                          CH                                                 F                                                                                       ##STR48##                                                                              OCH.sub.3                                                                         OCH.sub.3                                                                         CH                                                 CH.sub.3                                                                                ##STR49##                                                                              OCH.sub.3                                                                         OCH.sub.3                                                                         N                                                  OCH.sub.3                                                                               ##STR50##                                                                              OCH.sub.3                                                                         OCH.sub.3                                                                         N                                                  H                                                                                       ##STR51##                                                                              OCH.sub.3                                                                         OCH.sub.3                                                                         N                                                  H                                                                                       ##STR52##                                                                              OCH.sub.3                                                                         OCH.sub.3                                                                         N                                                  Cl                                                                                      ##STR53##                                                                              OCH.sub.3                                                                         OCH.sub.3                                                                         CH                                                 NO.sub.2                                                                                ##STR54##                                                                              OCH.sub.3                                                                         CH.sub.3                                                                          CH                                                 NO.sub.2                                                                                ##STR55##                                                                              OCH.sub.3                                                                         OCH.sub.3                                                                         CH                                                 NO.sub.2                                                                                ##STR56##                                                                              OCH.sub.3                                                                         CH.sub.3                                                                          N                                                  F                                                                                       ##STR57##                                                                              OCH.sub.3                                                                         OCH.sub.3                                                                         N                                                  F                                                                                       ##STR58##                                                                              OCH.sub.3                                                                         OCH.sub.3                                                                         N                                                  Cl                                                                                      ##STR59##                                                                              OCH.sub.3                                                                         OCH.sub.3                                                                         N                                                  Cl                                                                                      ##STR60##                                                                              OCH.sub.3                                                                         CH.sub.3                                                                          N                                                  Cl                                                                                      ##STR61##                                                                              OCH.sub.3                                                                         OCH.sub.3                                                                         N                                                  H                                                                                       ##STR62##                                                                              OCH.sub.3                                                                         OCH.sub.3                                                                         N                                                  H                                                                                       ##STR63##                                                                              OCH.sub.3                                                                         OCH.sub.3                                                                         N                                                  CH.sub.2 CH.sub.3                                                                      NHCON(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                         OCH.sub.3                                                                         CH                                                 CH(CH.sub.3).sub.2                                                                     NHCON(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                         OCH.sub.3                                                                         CH                                                 SO.sub.2 CH.sub.3                                                                      NHCON(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                         OCH.sub.3                                                                         CH                                                 SO.sub.2 CH.sub.2 CH.sub.3                                                             NHCON(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                         OCH.sub.3                                                                         CH                                                 SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                    NHCON(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                         OCH.sub.3                                                                         CH                                                 CH.sub.2 CH.sub.3                                                                      NHCONHCH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                         N                                                  CH(CH.sub.3).sub.2                                                                     NHCONHCH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                         N                                                  SO.sub.2 CH.sub.3                                                                      NHCONHCH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                         N                                                  SO.sub.2 CH.sub.2 CH.sub.3                                                             NHCONHCH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                         N                                                  SO.sub.2 CH.sub.2 CH.sub. 2 CH.sub.3                                                   NHCONHCH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3                                                                         N                                                  CH.sub.3 NHCONHCH.sub.3                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                         CH 216-218° C.                              CH.sub.3 NHCONHCH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          CH 188-190° C.                              __________________________________________________________________________

EXAMPLE 62-Amino-N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide

A suspension containing 1 g ofN-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-nitrobenzenesulfonamide,0.2 g of 5% palladium on carbon and 50 ml of ethanol was shaken in aPaar apparatus under 40 p.s.i.g. hydrogen at ambient temperature. Afterone hour, the reaction mixture was filtered and the solids therebyrecovered, which contained catalyst and desired product, was stirredwith 10% aqueous sodium hydroxide. Filtration of that mixture andacidification of the filtrate with hydrochloric acid to pH 3 caused thedesired product to precipitate. After removal by filtration and drying,the desired product melted at 212°-216° and showed infrared absorptionpeaks at 3200 and 3300 cm⁻¹, consistent for the desired amino-containingcompound. Mass spectrometry showed two particles of mass 198 and 123units, equivalent to aminobenzenesulfonyl isocyanate and2-amino-4,6-dimethylpyrimidine respectively, as expected for the desiredcompound.

EXAMPLE 72-Amino-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide

A suspension containing 2 g of the sodium salt ofN-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-nitrobenzenesulfonamide,25 ml of glacial acetic acid and 0.2 g of 10% palladium on carbon wasshaken in a Paar apparatus at 40 p.s.i.g. hydrogen at ambienttemperature. After twenty-four hours, no further pressure drop wasobserved. The reaction mixture was filtered and the filtrate stripped toyield a small amount of the desired product. The solids which containedmost of the product and catalyst, were stirred with 20 ml of 5% aqueoussodium hydroxide, filtered and the filtrate combined with the residuefrom the acetic acid filtrate. After refiltering the resultant alkalinesolution, it was acidified to pH 3 with dilute hydrochloric acid toprecipitate the desired compound. After filtration and drying, thecompound, when heated to 160°, underwent a transformation in physicalappearance and subsequently melted at 210°-215°. The infrared absorptionpressure for the compound showed absorption peaks at 3300 and 3400 cm⁻¹,consistent for an amino substituent, and absorption bands at 1700, 1690,1600 and 1550 cm⁻¹ which are consistent for the amino-carbonylsulfonamide function. The product thus obtained was sufficiently purefor the purposes of this invention.

EXAMPLE 7a5-Amino-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methylbenzenesulfonamide

A suspension containing 8 g ofN-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methyl-5-nitrobenzenesulfonamide,0.5 g of 10% palladium on carbon and 150 ml of glacial acetic acid wasshaken in a Paar apparatus under 40 p.s.i.g. hydrogen and ambienttemperature. After ten hours, no further pressure drop was observed. Theproduct, which was isolated as described in Example 7, melted withdecomposition at 160°. It was sufficiently pure for the purposes of thisinvention.

By using the procedure of Example 6, 7 or 7a with equivalent amounts ofan appropriate nitro-N-[(pyrimidin-2-yl)aminocarbonyl]benzenesulfonamideor nitro-N-[(1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide, thecompounds of Table IV can be prepared

                  TABLE IV                                                        ______________________________________                                         ##STR64##                                                                    R.sub.1    R.sub.2 X       Y     Z    m.p.                                    ______________________________________                                        H          2-NH.sub.2                                                                            CH.sub.3                                                                              CH.sub.3 O                                                                          N                                            H          2-NH.sub.2                                                                            CH.sub.3 O                                                                            CH.sub.3 O                                                                          CH   141-142° C.                      H          2-NH.sub.2                                                                            CH.sub.3 O                                                                            CH.sub.3 O                                                                          N                                            Cl         5-NH.sub.2                                                                            CH.sub.3 O                                                                            CH.sub.3                                                                            N                                            CH.sub.3 O 5-NH.sub.2                                                                            CH.sub.3 O                                                                            CH.sub.3                                                                            CH                                           F          5-NH.sub.2                                                                            CH.sub.3 O                                                                            CH.sub.3                                                                            N                                            Br         5-NH.sub.2                                                                            C.sub.2 H.sub.5 O                                                                     CH.sub.3 O                                                                          CH                                           CH.sub.3   5-NH.sub.2                                                                            CH.sub.3 O                                                                            CH.sub.3                                                                            N    204-213° C.                      CH.sub.3   5-NH.sub.2                                                                            CH.sub.3 O                                                                            CH.sub.3 O                                                                          CH   104-106° C.                      H          3-NH.sub.2                                                                            CH.sub.3 O                                                                            CH.sub.3                                                                            CH                                           H          3-NH.sub.2                                                                            CH.sub.3 O                                                                            CH.sub.3 O                                                                          CH                                           H          3-NH.sub.2                                                                            CH.sub.3                                                                              CH.sub.3                                                                            CH                                           H          3-NH.sub.2                                                                            CH.sub.3 O                                                                            CH.sub.3                                                                            N                                            H          3-NH.sub.2                                                                            CH.sub.3 O                                                                            CH.sub.3 O                                                                          N                                            Cl         5-NH.sub.2                                                                            CH.sub.3 O                                                                            CH.sub.3 O                                                                          CH                                           Cl         5-NH.sub.2                                                                            CH.sub.3 O                                                                            CH.sub.3                                                                            CH                                           CH.sub.3   5-NH.sub.2                                                                            CH.sub.3 O                                                                            CH.sub.3                                                                            CH   135-137° C.                      CH.sub.3   5-NH.sub.2                                                                            C.sub.2 H.sub.5 O                                                                     CH.sub.3                                                                            CH                                           H          2-NH.sub.2                                                                            CH.sub.3                                                                              CH.sub.3                                                                            N                                            H          2-NH.sub.2                                                                            CH.sub.3                                                                              CH.sub.3                                                                            CH                                           H          2-NH.sub.2                                                                            CH.sub.3                                                                              CH.sub.3 O                                                                          CH                                           CH.sub.3   5-NH.sub.2                                                                            CH.sub.3 O                                                                            CH.sub.3 O                                                                          N    205-212° C.                      CH.sub.3   5-NH.sub.2                                                                            C.sub.2 H.sub.5 O                                                                     CH.sub.3 O                                                                          CH                                           CH.sub.3   5-NH.sub.2                                                                            C.sub.2 H.sub.5 O                                                                     CH.sub.3                                                                            N                                            Cl         5-NH.sub.2                                                                            C.sub.2 H.sub.5 O                                                                     CH.sub.3                                                                            N                                            Cl         5-NH.sub.2                                                                            C.sub.2 H.sub.5 O                                                                     CH.sub.3                                                                            CH                                           Cl         5-NH.sub.2                                                                            C.sub.2 H.sub.5 O                                                                     CH.sub.3 O                                                                          CH                                           C.sub.2 H.sub.5                                                                          5-NH.sub.2                                                                            OCH.sub.3                                                                             CH.sub.3                                                                            CH                                           CH(CH.sub.3).sub.2                                                                       5-NH.sub. 2                                                                           OCH.sub.3                                                                             CH.sub.3                                                                            CH                                           CH.sub.2 CH.sub.2 CH.sub.3                                                               5-NH.sub.2                                                                            OCH.sub.3                                                                             CH.sub.3                                                                            CH                                           SO.sub.2 CH.sub.3                                                                        5-NH.sub.2                                                                            OCH.sub.3                                                                             CH.sub.3                                                                            CH                                           SO.sub.2 CH.sub.2 CH.sub.3                                                               5-NH.sub.2                                                                            OCH.sub.3                                                                             CH.sub.3                                                                            CH                                           SO.sub.2 CH(CH.sub.3).sub.2                                                              5-NH.sub.2                                                                            OCH.sub.3                                                                             CH.sub.3                                                                            CH                                           SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                      5-NH.sub.2                                                                            OCH.sub.3                                                                             CH.sub.3                                                                            CH                                           SO.sub.2 CH.sub.3                                                                        5-NH.sub.2                                                                            OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                           SO.sub.2 CH.sub.2 CH.sub.3                                                               5-NH.sub.2                                                                            OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                           SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                      5-NH.sub.2                                                                            OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                           C.sub.2 H.sub.5                                                                          5-NH.sub.2                                                                            OCH.sub.3                                                                             CH.sub.3                                                                            N                                            CH.sub.2 CH.sub.2 CH.sub.3                                                               5-NH.sub.2                                                                            OCH.sub.3                                                                             CH.sub.3                                                                            N                                            CH(CH.sub.3).sub.2                                                                       5-NH.sub.2                                                                            OCH.sub.3                                                                             CH.sub.3                                                                            N                                            SO.sub.2 CH.sub.3                                                                        5-NH.sub.2                                                                            OCH.sub.3                                                                             CH.sub.3                                                                            N                                            SO.sub.2 C.sub.2 H.sub.5                                                                 5-NH.sub.2                                                                            OCH.sub.3                                                                             CH.sub.3                                                                            N                                            SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                      5-NH.sub.2                                                                            OCH.sub.3                                                                             CH.sub.3                                                                            N                                            SO.sub.2 CH(CH.sub.3).sub.2                                                              5-NH.sub.2                                                                            OCH.sub.3                                                                             CH.sub.3                                                                            N                                            ______________________________________                                    

In accordance with the technique described by and for Equation 6, amidocompounds of this invention can be prepared. For example, the compoundof Example 7 can be converted to2-acetamido-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamideas follows.

To a solution of 3.4 g of2-amino-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamidein 200 ml of methylene chloride is added a solution prepared from 0.9 gof acetyl chloride, 0.9 g of pyridine, and 25 ml of methylene chloride.After stirring at ambient temperature for two days, the reaction mixtureis worked with an equal volume of water several times, dried overmagnesium sulfate, filtered and concentrated to yield the desiredcompound,2-acetamido-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide,which can be used without further purification for the purposes of thisinvention.

The compound of Example 7 can also be converted to2-acetamido-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamideby the method described in Equation 7A as shown in Example 8. By usingequivalent amounts of other appropriate aminobenzenesulfonamidesadditional compounds of Formula I set forth in Table V can be preparedaccording to the method of Example 8.

EXAMPLE 82-Acetamido-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide

2-Amino-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide (1.0 g) suspended in 25 ml ofdichloromethane was treated with ketene for 10 minutes (ca. 0.4mole/hr). The mixture was allowed to stand and after 15 minutes a lightorange solution resulted. Evaporation of the solvent gave an orangeglassy oil which was triturated with water and allowed to stand for 16hours. The white solid thus obtained was removed by filtration and driedin-vacuo to yield 0.24 g of the desired product, m.p. 161°-162°. Theproduct showed absorption peaks by proton NMR at 4.0 (singlet, 3H); 2.5(singlet, 3H) and 2.1 (singlet, 3H) consistent for the acetylatedderivative. The infrared absorption spectrum showed peaks at 1700, 1695,1610 and 1580 also confirming the desired acylation.

By using equivalent amounts of an appropriate aminobenzenesulonamide andan appropriate anhydride, the compounds of Formula I set forth in TableV can be prepared in accordance with the procedure described by and forEquation 7. For example,5-acetamido-2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-3-yl)aminocarbonyl]benzenesulfonamidecan be prepared as follows.

To a solution of 37.3 g of5-amino-2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamideprepared in a minimum amount of boiling chloroform, is added withvigorous stirring 20.4 g of acetic anhydride. The resulting mixture isthen refluxed for 24 hours, the chloroform, excess acetic anhydride andacetic acid are removed in vacuo to yield as residue the desiredproduct,5-acetamido-2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide.

                  TABLE V                                                         ______________________________________                                         ##STR65##                                                                    R.sub.1    R.sub.2      X       Y    Zm.p.                                    ______________________________________                                        H          3-NHCOCH.sub.3                                                                             OCH.sub.3                                                                             OCH.sub.3                                                                          CH                                       H          3-NHCOCH.sub.3                                                                             OCH.sub.3                                                                             OCH.sub.3                                                                          N                                        H          3-NHCOCH.sub.3                                                                             OCH.sub.3                                                                             CH.sub.3                                                                           N                                        H          3-NHCOC.sub.2 H.sub.5                                                                      OC.sub.2 H.sub.5                                                                      CH.sub.3                                                                           N                                        Cl         5-NHCOCH.sub.3                                                                             OCH.sub.3                                                                             OCH.sub.3                                                                          CH                                       Cl         5-NHCOC.sub.2 H.sub.5                                                                      OCH.sub.3                                                                             OCH.sub.3                                                                          N                                        Cl         5-NHCOCH.sub.3                                                                             OCH.sub.3                                                                             CH.sub.3                                                                           N                                        Cl         5-NHCOCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      CH.sub.3                                                                           N                                        CH.sub.3   5-NHCOC.sub.2 H.sub.5                                                                      OCH.sub.3                                                                             OCH.sub.3                                                                          CH                                       CH.sub.3   5-NHCOCH.sub.3                                                                             OCH.sub.3                                                                             OCH.sub.3                                                                          N                                        CH.sub.3   5-NHCOCH.sub.3                                                                             OCH.sub.3                                                                             CH.sub.3                                                                           N                                        CH.sub.3   5-NHCOCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      CH.sub.3                                                                           N                                        Br         5-NHCOC.sub.2 H.sub.5                                                                       OCH.sub.3                                                                            OCH.sub.3                                                                          CH                                       Br         5-NHCOCH.sub.3                                                                             OCH.sub.3                                                                             OCH.sub.3                                                                          N                                        Br         5-NHCOCH.sub.3                                                                             OCH.sub.3                                                                             CH.sub.3                                                                           N                                        Br         5-NHCOCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      CH.sub.3                                                                           N                                        F          5-NHCOC.sub.2 H.sub.5                                                                      OC.sub.2 H.sub.5                                                                      OCH.sub.3                                                                          CH                                       F          5-NHCOC.sub.2 H.sub.5                                                                      OCH.sub.3                                                                             OCH.sub.3                                                                          N                                        F          5-NHCOC.sub.2 H.sub.5                                                                      OCH.sub.3                                                                             CH.sub.3                                                                           N                                        F          5-NHCOCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      OCH.sub.3                                                                          N                                        OCH.sub.3  5-NHCOCH.sub.3                                                                             OCH.sub.3                                                                             OCH.sub.3                                                                          CH                                       OCH.sub.3  5-NHCOCH.sub.3                                                                             OCH.sub.3                                                                             OCH.sub.3                                                                          N                                        OCH.sub.3  5-NHCOCH.sub.3                                                                             OCH.sub.3                                                                             CH.sub.3                                                                           N                                        OCH.sub.3  5-NHCOCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      OCH.sub.3                                                                          N                                        NO.sub.2   5-NHCOCH.sub.3                                                                             OCH.sub.3                                                                             OCH.sub.3                                                                          CH                                       NO.sub.2   5-NHCOCH.sub.3                                                                             OCH.sub.3                                                                             OCH.sub.3                                                                          N                                        NO.sub.2   5-NHCOCH.sub.3                                                                             OCH.sub.3                                                                             CH.sub.3                                                                           N                                        NO.sub.2   5-NHCOCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      OCH.sub.3                                                                          N                                        H          2-NHCO(n-C.sub.3 H.sub.7)                                                                  OCH.sub.3                                                                             OCH.sub.3                                                                          CH                                       H          2-NHCO(n-C.sub.3 H.sub.7)                                                                  OCH.sub.3                                                                             CH.sub.3                                                                           N                                        H          3-NHCO(n-C.sub.3 H.sub.7)                                                                  OC.sub.2 H.sub.5                                                                      CH.sub.3                                                                           N                                        Cl         5-NHCO(n-C.sub.3 H.sub.7)                                                                  OCH.sub.3                                                                             OCH.sub.3                                                                          CH                                       Cl         5-NHCO(n-C.sub.3 H.sub. -)                                                                 OCH.sub.3                                                                             OCH.sub.3                                                                          N                                        Cl         5-NHCO(n-C.sub.3 H.sub.7)                                                                  OCH.sub.3                                                                             CH.sub.3                                                                           N                                        Cl         5-NHCO(n-C.sub.3 H.sub.7)                                                                  OC.sub.2 H.sub.5                                                                      CH.sub.3                                                                           N                                        CH.sub.3   5-NHCO(n-C.sub.3 H.sub.7)                                                                  OCH.sub.3                                                                             OCH.sub.3                                                                          CH                                       CH.sub.3   5-NHCO(n-C.sub.3 H.sub.7)                                                                  OCH.sub.3                                                                             OCH.sub.3                                                                          N                                        Br         5-NHCO(n-C.sub.3 H.sub.7)                                                                  OC.sub.2 H.sub.5                                                                      CH.sub.3                                                                           CH                                       Br         5-NHCO(n-C.sub.3 H.sub.7)                                                                  OCH.sub.3                                                                             CH.sub.3                                                                           N                                        F          5-NHCO(n-C.sub.3 H.sub.7)                                                                  OCH.sub.3                                                                             OCH.sub.3                                                                          CH                                       F          5-NHCO(n-C.sub.3 H.sub.7)                                                                  OC.sub.2 H.sub.5                                                                      CH.sub.3                                                                           N                                        OCH.sub.3  5-NHCO(n-C.sub.3 H.sub.7)                                                                  OCH.sub.3                                                                             CH.sub.3                                                                           CH                                       OCH.sub.3  5-NHCO(n-C.sub.3 H.sub.7)                                                                  OC.sub.2 H.sub.5                                                                      CH.sub.3                                                                           N                                        NO.sub.2   5-NHCO(n-C.sub.3 H.sub.7)                                                                  OCH.sub.3                                                                             OCH.sub.3                                                                          CH                                       NO.sub.2   5-NHCO(n-C.sub.3 H.sub.7)                                                                  OCH.sub.3                                                                             OCH.sub.3                                                                          N                                        C.sub.2 H.sub.5                                                                          5-NHCOCH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                                                                          CH                                       CH(CH.sub.3).sub.2                                                                       5-NHCOCH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                                                                          CH                                       CH.sub.2 CH.sub.2 CH.sub.3                                                               5-NHCOCH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                                                                          CH                                       SO.sub.2 CH.sub.3                                                                        5-NHCOCH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                                                                          CH                                       SO.sub. 2 CH.sub.2 CH.sub.3                                                              5-NHCOCH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                                                                          CH                                       SO.sub.2 CH.sub.2 CH.sub.3                                                               5-NHCOCH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                                                                          CH                                       SO.sub.2 CH.sub.3                                                                        5-NHCOCH.sub.3                                                                             OCH.sub.3                                                                             OCH.sub.3                                                                          CH                                       SO.sub.2 CH.sub.2 CH.sub.3                                                               5-NHCOCH.sub.3                                                                             OCH.sub.3                                                                             OCH.sub.3                                                                          CH                                       SO.sub.2 CH(CH.sub.3).sub.2                                                              5-NHCOCH.sub.3                                                                             OCH.sub.3                                                                             OCH.sub.3                                                                          CH                                       C.sub.2 H.sub.5                                                                          3-NHCOCH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                                                                          N                                        CH(CH.sub.3).sub.2                                                                       5-NHCOCH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                                                                          N                                        CH.sub.2 CH.sub.2 CH.sub.3                                                               3-NHCOCH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                                                                          N                                        SO.sub.2 CH.sub.3                                                                        5-NHCOCH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                                                                          N                                        SO.sub.2 CH.sub.2 CH.sub.3                                                               5-NHCOCH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                                                                          N                                        SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                      5-NHCOCH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                                                                          N                                        SCH.sub.3  5-NHCOCH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                                                                          N                                        SCH.sub.2 CH.sub.3                                                                       5-NHCOCH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                                                                          N                                        SCH(CH.sub.3).sub.2                                                                      5-NHCOCH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                                                                          N                                        H          2-NHCOCH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                                                                           CH                                       H          2-NHCOCH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                                                                          CH161-                                                                        162° C.                           H          2-NHCOCH.sub.3                                                                             OCH.sub.3                                                                             OCH.sub.3                                                                          CH                                       H          2-NHCOCH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                                                                           N                                        H          2-NHCOCH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                                                                          N                                        H          2-NHCOCH.sub.3                                                                             OCH.sub.3                                                                             OCH.sub.3                                                                          N                                        ______________________________________                                    

By using the procedure of Equation 8 or 12 with equivalent amounts of anappropriate aminobenzenesulfonamide and an appropriate carbamoyl halideor chloroformate, the compounds of Formula I as set forth in Table VIcan be prepared. For example,2-dimethylureido-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl)benzenesulfonamidecan be prepared as follows.

A mixture containing 0.8 g of dimethylcarbamoyl chloride and 0.8 g ofpyridine is warmed to 80° on a steam bath for twenty minutes and thendiluted to 25 ml with methylene chloride. The above mixture is thenadded to 200 ml of methylene chloride containing 3.3 g of2-amino-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide.The mixture is stirred at reflux for one day, then washed thoroughlywith ice water, dried over magnesium sulfate, filtered and the solventdistilled off in vacuo to yield the desired product which issufficiently pure for the purposes of this invention.

                  TABLE VI                                                        ______________________________________                                         ##STR66##                                                                    R.sub.1    R.sub.2         X       Y   Z                                      ______________________________________                                        H          2-NHCO.sub.2 CH.sub.3                                                                         C.sub.2 H.sub.5 O                                                                     CH.sub.3  CH                               H          2-NHCO.sub.2 CH.sub.3                                                                         CH.sub.3 O                                                                            CH.sub.3 O CH                              H          2-NHCO.sub.2 CH.sub.3                                                                         CH.sub.3 O                                                                            CH.sub.3  N                                H          2-NHCO.sub.2 C.sub.2 H.sub.5                                                                  CH.sub.3 O                                                                            CH.sub.3 O N                               H          2-NHCO.sub.2 C.sub.2 H.sub.5                                                                  CH.sub.3 O                                                                            CH.sub.3  CH                               H          2-NHCO.sub.2 C.sub.2 H.sub.5                                                                  CH.sub.3 O                                                                            CH.sub.3  N                                            ##STR67##      CH.sub.3 O                                                                            CH.sub.3  N                                H                                                                                         ##STR68##      CH.sub.3 O                                                                            CH.sub.3  CH                               H                                                                                         ##STR69##      CH.sub.3 O                                                                            CH.sub.3 O CH                              H                                                                                         ##STR70##      CH.sub.3 O                                                                            CH.sub.3 O N                               H                                                                                         ##STR71##      CH.sub.3 O                                                                            CH.sub.3  N                                H                                                                                         ##STR72##      CH.sub.3 O                                                                            CH.sub.3  CH                               H                                                                                         ##STR73##      CH.sub.3 O                                                                            CH.sub.3 O N                               H                                                                                         ##STR74##      CH.sub.3 O                                                                            CH.sub.3  CH                               H                                                                                         ##STR75##      C.sub.2 H.sub.5 O                                                                     CH.sub.3 O N                               H                                                                                         ##STR76##      CH.sub.3 O                                                                            CH.sub.3  N                                H                                                                                         ##STR77##      CH.sub.3 O                                                                            CH.sub.3 O CH                              H                                                                                         ##STR78##      CH.sub.3 O                                                                            CH.sub.3  CH                               H                                                                                         ##STR79##      CH.sub.3 O                                                                            CH.sub.3  N                                H                                                                                         ##STR80##      CH.sub.3 O                                                                            CH.sub.3 O CH                              H                                                                                         ##STR81##      CH.sub.3 O                                                                            CH.sub.3  CH                               H                                                                                         ##STR82##      CH.sub.3 O                                                                            CH.sub.3  CH                               H                                                                                         ##STR83##      CH.sub.3 O                                                                            CH.sub.3 O CH                              H                                                                                         ##STR84##      CH.sub.3 O                                                                            CH.sub.3  N                                H                                                                                         ##STR85##      CH.sub.3 O                                                                            CH.sub.3  N                                H                                                                                         ##STR86##      CH.sub.3 O                                                                            CH.sub.3  CH                               CH.sub.3   5-NHCO.sub.2 CH.sub.3                                                                         CH.sub.3                                                                              OCH.sub.3  CH                              C.sub.2 H.sub.5                                                                          5-NHCO.sub.2 CH.sub.3                                                                         CH.sub.3                                                                              OCH.sub.3   CH                             CH.sub.2 CH.sub.2 CH.sub.3                                                               5-NHCO.sub.2 CH.sub.3                                                                         CH.sub.3                                                                              OCH.sub.3  CH                              SCH.sub.3  5-NHCO.sub.2 CH.sub.3                                                                         CH.sub.3                                                                              OCH.sub.3  CH                              SCH.sub.2 CH.sub.3                                                                       5-NHCO.sub.2 CH.sub.3                                                                         CH.sub.3                                                                              OCH.sub.3  CH                              SCH.sub.2 CH.sub.2 CH.sub.3                                                              5-NHCO.sub.2 CH.sub.3                                                                         CH.sub.3                                                                              OCH.sub.3  CH                              SO.sub.2 CH.sub.3                                                                        5-NHCO.sub.2 CH.sub.3                                                                         CH.sub.3                                                                              OCH.sub.3  CH                              SO.sub.2 CH.sub.2 CH.sub.3                                                               5-NHCO.sub.2 CH.sub.3                                                                         CH.sub.3                                                                              OCH.sub.3  CH                              SO.sub.2 CH.sub.3                                                                        5-NHCO.sub.2 CH.sub.3                                                                         CH.sub.3                                                                              OCH.sub.3  CH                              SO.sub.2 CH.sub.2 CH.sub.3                                                               5-NHCO.sub.2 CH.sub.3                                                                         CH.sub.3                                                                              OCH.sub.3  CH                              Cl         5-NHCO.sub.2 CH.sub.3                                                                         CH.sub.3                                                                              OCH.sub.3  CH                              F          5-NHCO.sub.2 CH.sub.3                                                                         CH.sub.3                                                                              OCH.sub.3  CH                              Br         5-NHCO.sub.2 CH.sub.3                                                                         CH.sub.3                                                                              OCH.sub.3  CH                              CF.sub.3   5-NHCO.sub.2 CH.sub.3                                                                         CH.sub.3                                                                              OCH.sub.3  CH                              NO.sub.2   5-NHCO.sub.2 CH.sub.3                                                                         CH.sub.3                                                                              OCH.sub.3  CH                              OCH.sub.3  5-NHCO.sub.2 CH.sub.3                                                                         CH.sub.3                                                                              OCH.sub.3  CH                              SCH.sub.3  5-NHCO.sub.2 CH.sub.3                                                                         CH.sub.3                                                                              OCH.sub.3  N                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                      5-NHCO.sub.2 CH.sub.3                                                                         CH.sub.3                                                                              OCH.sub.3  N                               SO.sub.2 CH.sub.3                                                                        5-NHCO.sub.2 CH.sub.3                                                                         OCH.sub.3                                                                             OCH.sub.3  N                               SO.sub.2 CH.sub.3                                                                        5-NHCO.sub.2 CH.sub.3                                                                         CH.sub.3                                                                              OCH.sub.3  N                               ______________________________________                                    

In addition to the compounds shown in the above table, other compoundswhich can be prepared according to the same processes are those of TableII and Table III wherein both R₄ and R₅ are other than hydrogen.

By using the procedure of Equation 9 with equivalent amounts of anappropriate aminobenzenesulfonamide and an appropriate alkyl isocyanate,the compounds of Table VII can be prepared. For example, methyl[2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]phenyl]carbamatecan be prepared as follows.

To an anhydrous solution containing 3.4 g of2-amino-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamideand 100 ml of methylene chloride is added 0.6 g of methyl isocyanatewith stirring at reflux. The reaction mixture is stirred for anadditional sixteen hours at reflux and then concentrated in vacuo toyield the desired compound in sufficient purity for the purposes of thisinvention.

                  TABLE VII                                                       ______________________________________                                         ##STR87##                                                                    R.sub.1    R.sub.2        X       Y     Z                                     ______________________________________                                                    ##STR88##     CH.sub.3                                                                              CH.sub.3                                                                            CH                                    H                                                                                         ##STR89##     CH.sub.3 O                                                                            CH.sub.3 O                                                                          CH                                    H                                                                                         ##STR90##     CH.sub.3 O                                                                            CH.sub.3                                                                            CH                                    H                                                                                         ##STR91##     CH.sub.3 O                                                                            CH.sub.3 O                                                                          N                                     H                                                                                         ##STR92##     CH.sub.3                                                                              CH.sub.3 O                                                                          N                                     H                                                                                         ##STR93##     CH.sub.3 O                                                                            CH.sub.3 O                                                                          CH                                    H                                                                                         ##STR94##     CH.sub.3 O                                                                            CH.sub.3                                                                            CH                                    H                                                                                         ##STR95##     CH.sub.3 O                                                                            CH.sub.3                                                                            CH                                    H                                                                                         ##STR96##     CH.sub.3 O                                                                            CH.sub.3                                                                            N                                     H                                                                                         ##STR97##     CH.sub.3 O                                                                            CH.sub.3 O                                                                          N                                     H                                                                                         ##STR98##     CH.sub.3 O                                                                            CH.sub.3                                                                            N                                     H                                                                                         ##STR99##     CH.sub.3 O                                                                            CH.sub.3                                                                            CH                                    H                                                                                         ##STR100##    C.sub.2 H.sub.5 O                                                                     CH.sub.3 O                                                                          CH                                    H                                                                                         ##STR101##    CH.sub.3 O                                                                            CH.sub.3                                                                            CH                                    H                                                                                         ##STR102##    CH.sub.3 O                                                                            CH.sub.3                                                                            N                                     H                                                                                         ##STR103##    CH.sub.3 O                                                                            CH.sub.3                                                                            CH                                    H                                                                                         ##STR104##    C.sub.2 H.sub.5 O                                                                     CH.sub.3 O                                                                          N                                     H                                                                                         ##STR105##    CH.sub.3 O                                                                            CH.sub.3                                                                            N                                     H                                                                                         ##STR106##    CH.sub.3 O                                                                            CH.sub.3                                                                            N                                     H                                                                                         ##STR107##    CH.sub.3 O                                                                            CH.sub.3                                                                            CH                                    Cl                                                                                        ##STR108##    OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                    Br                                                                                        ##STR109##    OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                    F                                                                                         ##STR110##    OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                    CF.sub.3                                                                                  ##STR111##    OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                    OCH.sub.3                                                                                 ##STR112##    OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                    NO.sub.2                                                                                  ##STR113##    OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                    CH.sub.3                                                                                  ##STR114##    OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                    CH(CH.sub.3)                                                                              ##STR115##    OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                    SCH.sub.3                                                                                 ##STR116##    OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                    SO.sub.2 CH.sub.3                                                                         ##STR117##    CH.sub.3                                                                              OCH.sub.3                                                                           CH                                    SO.sub.2 CH.sub.3                                                                         ##STR118##    OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                    SCH(CH.sub.3).sub.2                                                                       ##STR119##    OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                    SO.sub.2 CH.sub.2 CH.sub.3                                                                ##STR120##    OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       ##STR121##    OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                    CH(CH.sub.3).sub.2                                                                        ##STR122##    OCH.sub.3                                                                             CH.sub.3                                                                            N                                     SCH.sub.3                                                                                 ##STR123##    OCH.sub.3                                                                             CH.sub.3                                                                            N                                     SO.sub.2 CH.sub.3                                                                         ##STR124##    OCH.sub.3                                                                             CH.sub.3                                                                            N                                     SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       ##STR125##    OCH.sub.3                                                                             CH.sub.3                                                                            N                                     SO.sub.2 CH.sub.2 CH.sub.3                                                                ##STR126##    OCH.sub.3                                                                             CH.sub.3                                                                            N                                     ______________________________________                                    

By using the procedure of Equation 10 with equivalent amounts of anappropriate aminobenzenesulfonamide and an appropriate aldehyde, thecompounds of Table VIII can be prepared. For example,5-dimethylamino-2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamidecan be prepared as follows.

To an agitated solution of 3.7 g of5-amino-2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamideand 0.88 g of sodium cyanoborohydride in 50 ml of acetonitrile is added3 ml of formalin. To the reaction mixture is then added 1 ml of glacialacetic acid over a period of 10 minutes. The reaction is then stirred atroom temperature for 2 hours, another ml of glacial acetic acid is addedand stirring is continued for an additional 30 minutes. The reactionmixture is then poured into 50 ml of water, brought to pH 7 by theaddition of aqueous sodium hydroxide and extracted several times withmethylene chloride. The combined methylene chloride extracts are washedwith brine and dried over anhydrous magnesium sulfate. Evaporation ofthe solvent in vacuo yields the desired product,5-dimethylamino-2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide.

                  TABLE VIII                                                      ______________________________________                                         ##STR127##                                                                   R.sub.1     R.sub.2     X        Y      Z                                     ______________________________________                                        H           2-N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                              OCH.sub.3                                                                            CH                                    H           2-N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                              OCH.sub.3                                                                            N                                     H           2-N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                              CH.sub.3                                                                             N                                     H           3-N(CH.sub.3).sub.2                                                                       OC.sub.2 H.sub.5                                                                       CH.sub.3                                                                             N                                     Cl          5-N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                              OCH.sub.3                                                                            CH                                    Cl          5-N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                              CH.sub.3                                                                             N                                     Cl          5-N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                              OCH.sub.3                                                                            N                                     Cl          5-N(CH.sub.3).sub.2                                                                       OC.sub.2 H.sub.5                                                                       CH.sub.3                                                                             N                                     Br          5-N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                              CH.sub.3                                                                             CH                                    Br          5-N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                              CH.sub.3                                                                             N                                     Br          5-N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                              OCH.sub.3                                                                            N                                     Br          5-N(CH.sub.3).sub.2                                                                       OC.sub.2 H.sub.5                                                                       CH.sub.3                                                                             N                                     F           5-N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                              OCH.sub.3                                                                            N                                     OCH.sub.3   5-N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                              CH.sub.3                                                                             CH                                    OCH.sub.3   5-N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                              OCH.sub.3                                                                            N                                     OCH.sub.3   5-N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                              CH.sub.3                                                                             N                                     H           3-N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                              CH.sub.3                                                                             CH                                    H           3-N(CH.sub.3).sub.2                                                                       OC.sub.2 H.sub.5                                                                       OCH.sub.3                                                                            CH                                    H           3-N(CH.sub.3).sub.2                                                                       CH.sub.3 CH.sub.3                                                                             CH                                    H           3-N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                              CH.sub.3                                                                             N                                     NO.sub.2    5-N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                              OCH.sub.3                                                                            CH                                    NO.sub.2    5-N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                              OCH.sub.3                                                                            N                                     NO.sub.2    5-N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                              CH.sub.3                                                                             N                                     NO.sub.2    5-N(CH.sub.3).sub.2                                                                       OC.sub.2 H.sub.5                                                                       CH.sub.3                                                                             N                                     H           2-N(CH.sub.3).sub.2                                                                       CH.sub.3 CH.sub.3                                                                             N                                     H           2-N(CH.sub.3).sub.2                                                                       CH.sub.3 O                                                                             CH.sub.3                                                                             CH                                    H           2-N(CH.sub.3).sub.2                                                                       CH.sub.3 CH.sub.3                                                                             CH                                    CH.sub.3    5-N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                              OCH.sub.3                                                                            CH                                    CH.sub.3    5-N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                              OCH.sub.3                                                                            N                                     CH.sub.3    5-N(CH.sub.3).sub. 2                                                                      OCH.sub.3                                                                              CH.sub.3                                                                             N                                     CH.sub.3    5-N(CH.sub.3).sub.2                                                                       OC.sub.2 H.sub.5                                                                       CH.sub.3                                                                             N                                     H           3-N(n-C.sub.2 H.sub.5).sub.2                                                              OCH.sub.3                                                                              CH.sub.3                                                                             N                                     Cl          5-N(n-C.sub.3 H.sub.7).sub.2                                                              OCH.sub.3                                                                              OCH.sub.3                                                                            CH                                    Cl          5-N(n-C.sub.2 H.sub.5).sub.2                                                              OCH.sub.3                                                                              OCH.sub.3                                                                            N                                     Cl          5-N(n-C.sub.3 H.sub.7).sub.2                                                              OCH.sub.3                                                                              CH.sub.3                                                                             N                                     Cl          5-N(n-C.sub.3 H.sub.7).sub.2                                                              OC.sub.2 H.sub.5                                                                       CH.sub.3                                                                             N                                     Br          5-N(n-C.sub.2 H.sub.5).sub.2                                                              OCH.sub.3                                                                              CH.sub.3                                                                             CH                                    Br          5-N(n-C.sub.3 H.sub.7).sub.2                                                              OCH.sub.3                                                                              CH.sub.3                                                                             N                                     Br          5-N(n-C.sub.3 H.sub.7).sub.2                                                              OC.sub.2 H.sub.5                                                                       CH.sub.3                                                                             N                                     CH.sub.3    5-N(n-C.sub.2 H.sub.5).sub.2                                                              OCH.sub.3                                                                              OCH.sub.3                                                                            CH                                    CH.sub.3    5-N(n-C.sub.3 H.sub.7).sub.2                                                              OCH.sub.3                                                                              CH.sub.3                                                                             N                                     CH.sub.3    5-N(n-C.sub.3 H.sub.7).sub.2                                                              OC.sub.2 H.sub.5                                                                       CH.sub.3                                                                             N                                     F           5-N(n-C.sub.3 H.sub.7).sub.2                                                              OC.sub.2 H.sub.5                                                                       OCH.sub.3                                                                            N                                     OCH.sub.3   5-N(n-C.sub.3 H.sub.7).sub.2                                                              OCH.sub.3                                                                              CH.sub.3                                                                             CH                                    OCH.sub.3   5-N(n-C.sub.3 H.sub.7).sub.2                                                              OCH.sub.3                                                                              OCH.sub.3                                                                            N                                     OCH.sub.3   5-N(n-C.sub.2 H.sub.5).sub.2                                                              OC.sub.2 H.sub.5                                                                       OCH.sub.3                                                                            N                                     NO.sub.2    5-N(n-C.sub.3 H.sub.7).sub.2                                                              OCH.sub.3                                                                              OCH.sub.3                                                                            CH                                    NO.sub.2    5-N(n-C.sub.3 H.sub.7).sub.2                                                              OCH.sub.3                                                                              OCH.sub.3                                                                            N                                     NO.sub.2    5-N(n-C.sub.3 H.sub.7).sub.2                                                              OC.sub.2 H.sub.5                                                                       OCH.sub.3                                                                            N                                     H           3-NHCH.sub.3                                                                              OCH.sub.3                                                                              OCH.sub.3                                                                            CH                                    H           3-NHCH.sub.3                                                                              OCH.sub.3                                                                              CH.sub.3                                                                             N                                     H           3-NHC.sub.2 H.sub.5                                                                       OCH.sub.3                                                                              CH.sub.3                                                                             N                                     Cl          5-NHCH.sub.3                                                                              OCH.sub.3                                                                              CH.sub.3                                                                             CH                                    Cl          5-NHC.sub.2 H.sub.5                                                                       OCH.sub.3                                                                              OCH.sub.3                                                                            N                                     Cl          5-NHCH.sub.3                                                                              OCH.sub.3                                                                              CH.sub.3                                                                             N                                     Cl          5-NHCH.sub.3                                                                              OC.sub.2 H.sub.5                                                                       CH.sub.3                                                                             N                                     Br          5-NHCH.sub.3                                                                              OCH.sub.3                                                                              CH.sub.3                                                                             CH                                    Br          5-NHC.sub.2 H.sub.5                                                                       OCH.sub.3                                                                              OCH.sub.3                                                                            N                                     Br          5-NHC.sub.3 H.sub.7                                                                       OC.sub.2 H.sub.5                                                                       CH.sub.3                                                                             N                                     CH.sub.3    5-NHCH.sub.3                                                                              OCH.sub.3                                                                              OCH.sub.3                                                                            CH                                    CH.sub.3    5-NHCH.sub.3                                                                              OCH.sub.3                                                                              CH.sub.3                                                                             N                                     CH.sub.3    5-NHCH.sub.3                                                                              OC.sub.2 H.sub.5                                                                       CH.sub.3                                                                             N                                     F           5-NHCH.sub.3                                                                              OCH.sub.3                                                                              OCH.sub.3                                                                            CH                                    F           5-NHCH.sub.3                                                                              OCH.sub.3                                                                              CH.sub.3                                                                             N                                     F           5-NHCH.sub.3                                                                              OC.sub.2 H.sub.5                                                                       CH.sub.3                                                                             N                                     OCH.sub.3   5-NHCH.sub.3                                                                              OCH.sub.3                                                                              OCH.sub.3                                                                            CH                                    OCH.sub.3   5-NHCH.sub.3                                                                              OCH.sub.3                                                                              CH.sub.3                                                                             N                                     OCH.sub.3   5-NHCH.sub.3                                                                              OC.sub.2 H.sub.5                                                                       CH.sub.3                                                                             N                                     NO.sub.2    5-NHCH.sub.3                                                                              OCH.sub.3                                                                              CH.sub.3                                                                             N                                     NO.sub.2    5-NHCH.sub.3                                                                              OCH.sub.3                                                                              CH.sub.3                                                                             CH                                    NO.sub.2    5-NHCH.sub.3                                                                              OC.sub.2 H.sub.5                                                                       CH.sub.3                                                                             N                                     C.sub.2 H.sub.5                                                                           5-NHCH.sub.3                                                                              OCH.sub.3                                                                              OCH.sub.3                                                                            CH                                    CH(CH.sub.3).sub.2                                                                        5-NHCH.sub.3                                                                              OCH.sub.3                                                                              OCH.sub.3                                                                            CH                                    SCH.sub.3   5-NHCH.sub.3                                                                              OCH.sub.3                                                                              OCH.sub.3                                                                            CH                                    SO.sub.2 CH.sub.3                                                                         5-NHCH.sub.3                                                                              OCH.sub.3                                                                              OCH.sub.3                                                                            CH                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       5-NHCH.sub.3                                                                              OCH.sub.3                                                                              OCH.sub.3                                                                            CH                                    SO.sub.2 CH(CH.sub.3).sub.2                                                               5-NHCH.sub.3                                                                              OCH.sub.3                                                                              OCH.sub.3                                                                            CH                                    C.sub.2 H.sub.5                                                                           5-N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                              CH.sub.3                                                                             N                                     CH.sub.2 CH.sub.2 CH.sub.3                                                                5-N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                              CH.sub.3                                                                             N                                     SO.sub.2 CH.sub.3                                                                         5-N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                              CH.sub.3                                                                             N                                     SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       5-N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                              CH.sub.3                                                                             N                                     SO.sub.2 CH.sub.3                                                                         5-N(CH.sub.3).sub.2                                                                       OCH.sub.3                                                                              CH.sub. 3                                                                            N                                     ______________________________________                                    

By using the procedure of Equation 11 with equivalent amounts of anappropriate benzenesulfonyl isocyanate and an appropriate2-aminopyrimidine or 2-amino-1,3,5-triazine, the compounds of Table IXcan be prepared. For example,2-chloro-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-5-pyrrolidinobenzenesulfonamidecan be prepared as follows.

To a suspension of 1.4 g of 2-amino-4-methoxy-6-methylpyrimidine in 50ml of methylene chloride is added with stirring 2.9 g of2-chloro-5-pyrrolidinobenzenesulfonyl isocyanate dissolved in 25 ml ofmethylene chloride at ambient temperature and pressure. After stirringovernight, the solvent is removed in vacuo. The residue thus obtained isthe desired2-chloro-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-5-pyrrolidinobenzenesulfonamidewhich may be used for the purposes of this invention without furtherpurification. Its purity can be improved by trituration with butylchloride and filtration.

                  TABLE IX                                                        ______________________________________                                         ##STR128##                                                                   R.sub.1     R.sub.2     X        Y      Z                                     ______________________________________                                                     ##STR129## CH.sub.3 O                                                                             CH.sub.3                                                                             CH                                    H                                                                                          ##STR130## CH.sub.3 O                                                                             CH.sub.3 O                                                                           CH                                    H                                                                                          ##STR131## CH.sub.3 O                                                                             CH.sub.3                                                                             N                                     H                                                                                          ##STR132## CH.sub.3 O                                                                             CH.sub.3 O                                                                           N                                     H                                                                                          ##STR133## CH.sub.3 O                                                                             CH.sub.3                                                                             N                                     H                                                                                          ##STR134## CH.sub.3 O                                                                             CH.sub.3                                                                             CH                                    Cl                                                                                         ##STR135## CH.sub.3 O                                                                             CH.sub.3                                                                             N                                     Cl                                                                                         ##STR136## CH.sub.3 O                                                                             CH.sub.3                                                                             CH                                    Cl                                                                                         ##STR137## CH.sub.3 O                                                                             CH.sub.3 O                                                                           CH                                    CH.sub.3                                                                                   ##STR138## CH.sub.3 O                                                                             CH.sub.3                                                                             N                                     CH.sub.3                                                                                   ##STR139## CH.sub.3 O                                                                             CH.sub.3                                                                             CH                                    CH.sub.3 O                                                                                 ##STR140## CH.sub.3 O                                                                             CH.sub.3                                                                             N                                     CH.sub.3 O                                                                                 ##STR141## CH.sub.3 O                                                                             CH.sub.3                                                                             CH.sub.3                              NO.sub.2                                                                                   ##STR142## CH.sub.3 O                                                                             CH.sub.3                                                                             CH                                    NO.sub.2                                                                                   ##STR143## CH.sub.3 O                                                                             CH.sub.3 O                                                                           N                                     NO.sub.2                                                                                   ##STR144## CH.sub.3 O                                                                             CH.sub.3                                                                             N                                     C.sub.2 H.sub.5                                                                            ##STR145## OCH.sub.3                                                                              OCH.sub.3                                                                            CH                                    CH(CH.sub.3).sub.2                                                                         ##STR146## OCH.sub.3                                                                              OCH.sub.3                                                                            CH                                    SO.sub.2 CH.sub.3                                                                          ##STR147## OCH.sub.3                                                                              OCH.sub.3                                                                            CH                                    SCH.sub.3                                                                                  ##STR148## OCH.sub.3                                                                              OCH.sub.3                                                                            CH                                    SO.sub.2 CH.sub.3                                                                          ##STR149## CH.sub.3 OCH.sub.3                                                                            CH                                    SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        ##STR150## OCH.sub.3                                                                              OCH.sub.3                                                                            CH                                    SO.sub.2 CH.sub.3                                                                          ##STR151## CH.sub.3 OCH.sub.3                                                                            N                                     SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        ##STR152## CH.sub.3 OCH.sub.3                                                                            N                                     SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        ##STR153## OCH.sub.3                                                                              OCH.sub.3                                                                            N                                     SO.sub.2 CH.sub.3                                                                          ##STR154## OCH.sub.3                                                                              OCH.sub.3                                                                            N                                     SCH.sub.3                                                                                  ##STR155## CH.sub.3 OCH.sub.3                                                                            N                                     CH(CH.sub.3).sub.2                                                                         ##STR156## CH.sub.3 OCH.sub.3                                                                            N                                     CH.sub.2 CH.sub.3                                                                          ##STR157## CH.sub.3 OCH.sub.3                                                                            N                                     ______________________________________                                    

Additional compounds wherein R₆ and R₇ are both other than hydrogen,which can be prepared by this method are shown in Table VIII.

EXAMPLE 92-Amino-N-[(4-methoxy-6-methyl-2-pyrimidinyl)aminocarbonyl]benzenesulfonamide--Sodiumsalt

To a suspension of 50 mg of2-amino-N-[(4-methoxy-6-methyl-2-pyrimidinyl)aminocarbonyl]benzenesulfonamidein 3 ml of methanol was added a solution of 10 mg of sodium methoxide in2 ml of methanol. The resulting clear solution was gently heated on asteam bath for 5 minutes and the solvent removed in vacuo to yield aglass. Trituration with 5 ml of ethylacetate followed by gentle heatingand filtration yields the sodium salt of2-amino-N-[(4-methoxy-6-methyl-2-pyrimidinyl)aminocarbonyl)benzenesulfonamide,m.p. 224-225 (dec.).

Following the procedure given in Example 9 the compounds in Table X canbe prepared.

                  TABLE X                                                         ______________________________________                                         ##STR158##                                                                   R.sub.1                                                                             R.sub.2     X        Y      Z     M.sup.+                                                                            n                                ______________________________________                                        NH.sub.2                                                                            H           CH.sub.3 OCH.sub.3                                                                            CH    Na   1                                NH.sub.2                                                                            H           CH.sub.3 CH.sub.3                                                                             CH    Na   1                                NH.sub.2                                                                            H           CH.sub.3 OCH.sub.3                                                                            N     K    1                                NH.sub.2                                                                            H           CH.sub.3 OCH.sub.3                                                                            N     Li   1                                Cl    NH.sub.2    OCH.sub.3                                                                              CH.sub.3                                                                             CH    K    1                                Cl    NH.sub.2    CH.sub.3 OCH.sub.3                                                                            N     Na   1                                Cl    NH.sub.2    OCH.sub.3                                                                              OCH.sub.3                                                                            N     Na   1                                Cl    NH.sub.2    OCH.sub.3                                                                              OCH.sub.3                                                                            N     Ca   2                                Cl    NH.sub.2    CH.sub.3 OCH.sub.3                                                                            CH    Li   1                                H     NHCO.sub.2 CH.sub. 3                                                                      OCH.sub.3                                                                              OCH.sub.3                                                                            N     Na   1                                H     NHCO.sub.2 CH.sub.3                                                                       OCH.sub.3                                                                              OCH.sub.3                                                                            N     Ca   2                                H     NHCO.sub.2 CH.sub.3                                                                       OCH.sub.3                                                                              CH.sub.3                                                                             N     Na   1                                H     NHCO.sub.2 CH.sub.3                                                                       OCH.sub.3                                                                              OCH.sub.3                                                                            CH    Li   1                                H     NHCO.sub.2 CH.sub.3                                                                       OCH.sub.3                                                                              OCH.sub.3                                                                            CH    K    1                                H     NHCO.sub.2 CH.sub.3                                                                       OCH.sub.3                                                                              CH.sub.3                                                                             CH    Na   1                                H     NHCO.sub.2 CH.sub.3                                                                       OCH.sub.3                                                                              CH.sub.3                                                                             CH    Li   1                                       ##STR159## OCH.sub.3                                                                              CH.sub.3                                                                             CH    Na   1                                H                                                                                    ##STR160## CH.sub.3 CH.sub.3                                                                             CH    Na   1                                H                                                                                    ##STR161## CH.sub.3 CH.sub.3                                                                             CH    Ca   2                                H                                                                                    ##STR162## OCH.sub.3                                                                              OCH.sub.3                                                                            N     K    1                                ______________________________________                                    

EXAMPLE 102-Amino-N-[(4-methoxy-6-methyl-2-pyrimidinyl)aminocarbonyl]benzenesulfonamide--Hydrochloride

A suspension of 56 mg of2-amino-N-[(4-methoxy-6-methyl-2-pyrimidinyl)aminocarbonyl]benzenesulfonamidein 5 ml of ethanolic HCl was gently heated on a steam bath for 5minutes. The resulting white suspension was evaporated in vacuo to yieldthe hydrochloride m.p. 154-155 (dec.).

Following the procedure given in Example 10, the compounds of Table XIcan be prepared.

                                      TABLE XI                                    __________________________________________________________________________     ##STR163##                                                                   R.sub.1 R.sub.6                                                                           R.sub.7                                                                          X   Y   Z  A         n                                         __________________________________________________________________________    H       H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH Cl        1                                         H       CH.sub.3                                                                          CH.sub.3                                                                         CH.sub.3                                                                          CH.sub.3                                                                          CH Br        1                                         H       H   H  CH.sub.3                                                                          OCH.sub.3                                                                         CH Cl        1                                         H       CH.sub.3                                                                          CH.sub.3                                                                         CH.sub.3                                                                          OCH.sub.3                                                                         CH CCl.sub.3 CO.sub.2                                                                      1                                         H       H   H  OCH.sub.3                                                                         OCH.sub.3                                                                         N  n-C.sub.12 H.sub.25 SO.sub.3                                                            1                                         H       H   CH.sub.3                                                                         OCH.sub.3                                                                         OCH.sub.3                                                                         N  Br        1                                         H       H   H  CH.sub.3                                                                          OCH.sub.3                                                                         N  Cl        1                                         H       CH.sub.3                                                                          H  CH.sub.3                                                                          OCH.sub.3                                                                         N  p(CH.sub.3)C.sub.2 H.sub.4 SO.sub.3                                                     1                                         Cl      H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH Cl        1                                         Cl      CH.sub.3                                                                          CH.sub.3                                                                         CH.sub.3                                                                          CH.sub.3                                                                          CH SO.sub.4  2                                         Cl      H   H  CH.sub.3                                                                          OCH.sub.3                                                                         CH Cl        1                                         Cl      H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH NO.sub.3  1                                         SO.sub.2 CH.sub.3                                                                     H   H  OCH.sub.3                                                                         OCH.sub.3                                                                         N  n-C.sub.12 H.sub.25 SO.sub.3                                                            1                                         SO.sub.2 CH.sub.2 CH.sub.3                                                            CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.3                                                                         OCH.sub.3                                                                         N  Br        1                                         CH.sub.2 CH.sub.3                                                                     H   H  OCH.sub.3                                                                         CH.sub.3                                                                          N  HPO.sub.4 2                                         CH(CH.sub.3).sub.2                                                                    C.sub.3 H.sub.7                                                                   C.sub.3 H.sub.7                                                                  OCH.sub.3                                                                         CH.sub.3                                                                          N  HSO.sub.4 1                                         Cl      CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.3                                                                         CH.sub.3                                                                          N  CCl.sub.3 CO.sub.2                                                                      1                                         Br      H   H  CH.sub.3                                                                          OCH.sub.3                                                                         CH Cl        1                                         Br      C.sub.2 H.sub.5                                                                   C.sub.2 H.sub.5                                                                  CH.sub.3                                                                          OCH.sub.3                                                                         CH p(CH.sub.3)C.sub.6 H.sub.4 SO.sub.3                                                     1                                         Br      H   H  CH.sub.3                                                                          OCH.sub.3                                                                         N  n-C.sub.12 H.sub.25 SO.sub.3                                                            1                                         Br      C.sub.2 H.sub.5                                                                   H  CH.sub.3                                                                          OCH.sub. 3                                                                        N  Cl        1                                         F       H   H  CH.sub.3                                                                          OCH.sub.3                                                                         CH SO.sub.4  2                                         F       CH.sub.3                                                                          CH.sub.3                                                                         CH.sub.3                                                                          OCH.sub.3                                                                         CH HSO.sub.4 1                                         F       H   H  OCH.sub.3                                                                         OCH.sub.3                                                                         N  Cl        1                                         F       C.sub.3 H.sub.7                                                                   C.sub.3 H.sub.7                                                                  OCH.sub.3                                                                         OCH.sub.3                                                                         N  CCl.sub.3 CO.sub.2                                                                      1                                         CH.sub.3                                                                              H   H  CH.sub.3                                                                          OCH.sub.3                                                                         CH Cl        1                                         CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                         CH.sub.3                                                                          OCH.sub.3                                                                         CH Br        1                                         CH.sub.3                                                                              H   H  CH.sub.3                                                                          OCH.sub.3                                                                         N  n-C.sub.12 H.sub.25 SO.sub.3                                                            1                                         CH.sub.3                                                                              CH.sub.3                                                                          H  CH.sub.3                                                                          OCH.sub.3                                                                         N  CH.sub.3 CO.sub.2                                                                       1                                         CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                         CH.sub.3                                                                          OCH.sub.3                                                                         CH Br        1                                         OCH.sub.3                                                                             H   H  CH.sub.3                                                                          CH.sub.3                                                                          CH Cl        1                                         OCH.sub.3                                                                             CH.sub.3                                                                          CH.sub.3                                                                         CH.sub.3                                                                          CH.sub.3                                                                          CH Br        1                                         OCH.sub.3                                                                             H   H  CH.sub.3                                                                          OCH.sub.3                                                                         N  Cl        1                                         OCH.sub.3                                                                             C.sub.2 H.sub.5                                                                   C.sub.2 H.sub.5                                                                  CH.sub.3                                                                          OCH.sub.3                                                                         N  pCH.sub.3 C.sub.6 H.sub.4 SO.sub.3                                                      1                                         __________________________________________________________________________

EXAMPLE 112-Amino-N-[(4-methoxy-6-methyl-2-pyrimidinyl)aminocarbonyl]benzenesulfonamide--Triethanolaminesalt

To a suspension of 1 g of2-amino-N-[(4-methoxy-6-methyl-2-pyrimidinyl)aminocarbonyl]benzenesulfonamidein 25 ml of methylene chloride is added 0.44 g of triethanolamine. Thesolvent is removed under reduced pressure to yield2-amino-N-[(4-methoxy-6-methyl-2-pyrimidinyl)aminocarbonyl]benzenesulfonamidetriethanolammonium salt.

According to the procedure given in Example 11 the compounds in TableXII can be prepared.

    __________________________________________________________________________    R.sub.1                                                                          R.sub.2  R.sub.8                                                                             R.sub.9                                                                          R.sub.10                                                                          X    Y   Z                                           __________________________________________________________________________    Cl 5-NH.sub.2                                                                             C.sub.6 H.sub.5                                                                     H  H   OCH.sub.3                                                                          CH.sub.3                                                                          CH                                          H  2-NHCO.sub.2 CH.sub.3                                                                  C.sub.6 H.sub.5                                                                     CH.sub.3                                                                         H   OCH.sub.3                                                                          CH.sub.3                                                                          N                                           H  3-NHCO.sub.2 CH.sub.3                                                                  C.sub.6 H.sub.5                                                                     CH.sub.3                                                                         CH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                                                         N                                           NH.sub.2                                                                         H        n-C.sub.12 H.sub.25                                                                 H  H   CH.sub.3                                                                           OCH.sub.3                                                                         N                                           Cl 5NH.sub.2                                                                               ##STR164##  OCH.sub.3                                                                          CH.sub.3                                                                          N                                           __________________________________________________________________________

                                      TABLE XII                                   __________________________________________________________________________     ##STR165##                                                                   R.sub.1                                                                          R.sub.2  R.sub.8                                                                              R.sub.9 R.sub.10                                                                              X   Y   Z                                  __________________________________________________________________________    NH.sub.2                                                                         H        H      CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                                                          OCH.sub.3                                                                         CH                                 NH.sub.2                                                                         H        H      CH.sub.2 CH.sub.2 OH                                                                  CH.sub.2 CH.sub.2 OH                                                                  CH.sub.3                                                                          CH.sub.3                                                                          CH                                 NH.sub.2                                                                         H        CH.sub.2 CH.sub.2 OH                                                                 CH.sub.2 CH.sub.2 OH                                                                  CH.sub.2 CH.sub.2 OH                                                                  CH.sub.3                                                                          OCH.sub.3                                                                         N                                  NH.sub.2                                                                         H        H      H       CH(CH.sub.3).sub.2                                                                    CH.sub.3                                                                          OCH.sub.3                                                                         N                                  Cl 5-NH.sub.2                                                                             H      H       H       OCH.sub.3                                                                         CH.sub.3                                                                          CH                                 Cl 5-NH.sub.2                                                                             H      CH.sub.2 CH.sub.2 OH                                                                  CH.sub.2 CH.sub.2 OH                                                                  CH.sub.3                                                                          OCH.sub.3                                                                         N                                  Cl 5-NH.sub.2                                                                             CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                                                                              OCH.sub.3                                                                         OCH.sub.3                                                                         N                                  Cl 5-NH.sub.2                                                                             C.sub.12 H.sub.25                                                                    H       H       OCH.sub.3                                                                         OCH.sub.3                                                                         N                                  Cl 5-NH.sub.2                                                                             H      CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                                                          OCH.sub.3                                                                         CH                                 H  2-NHCO.sub.2 CH.sub.3                                                                  CH.sub.2 CH.sub.2 OH                                                                 CH.sub.2 CH.sub.2 OH                                                                  CH.sub.2 CH.sub.2 OH                                                                  OCH.sub.3                                                                         OCH.sub.3                                                                         N                                  H  2-NHCO.sub.2 CH.sub.3                                                                  C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                       OCH.sub.3                                                                         OCH.sub.3                                                                         N                                  H  3-NHCO.sub.2 CH.sub.3                                                                  H      CH.sub.3                                                                              CH.sub.3                                                                              OCH.sub.3                                                                         CH.sub.3                                                                          N                                  H  3-NHCO.sub.2 CH.sub.3                                                                  H      H       H       OCH.sub.3                                                                         OCH.sub.3                                                                         CH                                 H  3-NHCO.sub.2 CH.sub.3                                                                  CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                                                                              OCH.sub.3                                                                         OCH.sub.3                                                                         CH                                 H  2-NHCO.sub.2 CH.sub.3                                                                  H      H       CH(CH.sub.3).sub.2                                                                    OCH.sub.3                                                                         CH.sub.3                                                                          CH                                 H  NHCO.sub.2 CH.sub.3                                                                    H      CH.sub.3                                                                              CH.sub.3                                                                              OCH.sub.3                                                                         CH.sub.3                                                                          CH                                     ##STR166##                                                                             ##STR167##            OCH.sub.3                                                                         CH.sub.3                                                                          CH                                 H                                                                                 ##STR168##                                                                            CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                                                          CH.sub.3                                                                          CH                                 H                                                                                 ##STR169##                                                                            H      C.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                       CH.sub.3                                                                          CH.sub.3                                                                          CH                                 H                                                                                 ##STR170##                                                                            C.sub.12 H.sub.25                                                                    H       H       OCH.sub.3                                                                         OCH.sub.3                                                                         N                                  __________________________________________________________________________

Formulations

Useful formulations of the compounds of Formula I can be prepared inconventional ways. They include dusts, granules, pellets, solutions,suspension, emulsions, wettable powders, emulsifiable concentrates andthe like. Many of these may be applied directly. Sprayable formulationscan be extended in suitable media and used at spray volumes of from afew liters to several hundred liters per hectare. High strengthcompositions are primarily used as intermediates for furtherformulation. The formulations, broadly, contain about 0.1% to 99% byweight of active ingredient(s) and at least one of (a) about 0.1% to 20%surfactant(s) and (b) about 1% to 99.9% solid or liquid diluent(s). Morespecifically, they will contain these ingredients in the followingapproximate proportions:

                  TABLE XIII                                                      ______________________________________                                                    Active  Weight Percent*                                                       Ingredient                                                                            Diluent(s)                                                                              Surfactant(s)                                   ______________________________________                                        Wettable Powders                                                                            20-90      0-74     1-10                                        Oil Suspensions,                                                                             3-50     40-95     0-15                                        Emulsions, Solutions,                                                         (including Emulsifiable                                                       Concentrates)                                                                 Aqueous Suspension                                                                          10-50     40-84     1-20                                        Dusts          1-25     70-99     0-5                                         Granules and Pellets                                                                        0.1-95      5-99.9  0-15                                        High Strength 90-99      0-10     0-2                                         Compositions                                                                  ______________________________________                                         *Active ingredient plus at least one of a Surfactant or a Diluent equals      100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be presentdepending on the intended use and the physical properties of thecompound. Higher ratios of surfactant to active ingredient are sometimesdesirable, and are achieved by incorporation into the formulation or bytank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook ofInsecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books,Caldwell, N.J., but other solids, either mined or manufactured, may beused. The more absorptive diluents are preferred for wettable powdersand the denser ones for dusts. Typical liquid diluents and solvents aredescribed in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York,1950. Solubility under 0.1% is preferred for suspension concentrates;solution concentrates are preferably stable against phase separation at0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC PublishingCorp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia ofSurface Active Agents", Chemical Publishing Co., Inc., N.Y., 1964, listsurfactants and recommended uses. All formulations can contain minoramounts of additives to reduce foaming, caking, corrosion,microbiological growth, etc.

The methods of making such compositions are well known. Solutions areprepared by simply mixing the ingredients. Fine solid compositions aremade by blending and, usually, grinding as in a hammer or fluid energymill. Suspensions are prepared by wet milling (see, for example,Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made byspraying the active material upon preformed granular carriers or byagglomeration techniques. See J. E. Browning, "Agglomeration", ChemicalEngineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer'sHandbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.

For further information regarding the art of formulation, see forexample:

H. M. Loux, U.S. Pat. No. 3,235,361, February 15, 1966, Col. 6, line 16through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, March 14, 1967, Col. 5, line43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58,132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3,line 66 through Col. 5, line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley & Sons, Inc.,New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., BlackwellScientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwiseindicated.

EXAMPLE 12

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        (1-Methylethyl) [3-[[(4-methoxy-6-methylpyrimidin-2-                          yl)aminocarbonyl]aminosulfonyl]phenyl]-                                       carbamate                    80%                                              sodium alkylnaphthalenesulfonate                                                                           2%                                               sodium ligninsulfonate       2%                                               synthetic amorphous silica   3%                                               kaolinite                    13%                                              ______________________________________                                    

The ingredients are blended, hammer-milled until all the solids areessentially under 50 microns, reblended, and packaged.

EXAMPLE 13

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        3-(3,3-dimethylureido)-N-[(4-methoxy-6-methylpyrimidin-                       2-yl)aminocarbonyl]benzenesulfonamide                                                                      50%                                              sodium alkylnaphthalenesulfonate                                                                           2%                                               low viscosity methyl cellulose                                                                             2%                                               diatomaceous earth           46%                                              ______________________________________                                    

The ingredients are blended, coarsely hammer-milled and then air-milledto produce particles essentially all below 10 microns in diameter. Theproduct is reblended before packaging.

EXAMPLE 14

    ______________________________________                                        Granule                                                                       ______________________________________                                        Wettable Powder of Example 13                                                                         5%                                                    attapulgite granules   95%                                                    (U.S.S. 20-40 mesh; 0.84-0.42 mm)                                             ______________________________________                                    

A slurry of wettable powder containing 25% solids is sprayed on thesurface of attapulgite granules in a double-cone blender. The granulesare dried and packaged.

EXAMPLE 15

    ______________________________________                                        Extruded Pellet                                                               ______________________________________                                        Methyl 3-[[(4-methoxy-6-methylpyrimidin-2-yl)amino-                           carbonyl]aminosulfonyl]phenyl]carbamate                                                                   25%                                               anhydrous sodium sulfate    10%                                               crude calcium ligninsulfonate                                                                              5%                                               sodium alkylnaphthalenesulfonate                                                                           1%                                               calcium/magnesium bentonite 59%                                               ______________________________________                                    

The ingredients are blended, hammer-milled and then moistened with about12% water. The mixture is extruded as cylinders about 3 mm diameterwhich are cut to produce pellets about 3 mm long. These may be useddirectly after drying, or the dried pellets may be crushed to pass aU.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S.No. 40 sieve (0.42 mm openings) may be packaged for use and the finesrecycled.

EXAMPLE 16

    ______________________________________                                        Oil Suspension                                                                ______________________________________                                        5-amino-N--[(4,6-dimethoxy-1,3,5-triazin-2-yl)amino-                          carbonyl]-2-methylbenzenesulfonamide                                                                        25%                                             polyoxyethylene sorbitol hexaoleate                                                                          5%                                             highly aliphatic hydrocarbon oil                                                                            70%                                             ______________________________________                                    

The ingredients are ground together in a sand mill until the solidparticles have been reduced to under about 5 microns. The resultingthick suspension may be applied directly, but preferably after beingextended with oils or emulsified in water.

EXAMPLE 17

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        5-amino-N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-                      2-methylbenzenesulfonamide    20%                                             sodium alkylnaphthalenesulfonate                                                                             4%                                             sodium ligninsulfonate         4%                                             low viscosity methyl cellulose                                                                               3%                                             attapulgite                   69%                                             ______________________________________                                    

The ingredients are thoroughly blended. After grinding in a hammer-millto produce particles essentially all below 100 microns, the material isreblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) andpackaged.

EXAMPLE 18

    ______________________________________                                        Low Strength Granule                                                          ______________________________________                                        5-amino-N--[(4-methoxy-6-methylpyrimidin-2-yl)amino-                          carbonyl]-2-methylbenzenesulfonamide                                                                       1%                                               N,N--dimethylformamide       9%                                               attapulgite granules         90%                                              (U.S.S. 20-40 sieve)                                                          ______________________________________                                    

The active ingredient is dissolved in the solvent and the solution issprayed upon dedusted granules in a double cone blender. After sprayingof the solution has been completed, the blender is allowed to run for ashort period and then the granules are packaged.

EXAMPLE 19

    ______________________________________                                        Aqueous Suspension                                                            ______________________________________                                        5-amino-N--[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-                       2-methylbenzenesulfonamide   40%                                              polyacrylic acid thickener   0.3%                                             dodecylphenol polyethylene glycol ether                                                                    0.5%                                             disodium phosphate           1%                                               monosodium phosphate         0.5%                                             polyvinyl alcohol            1.0%                                             water                        56.7%                                            ______________________________________                                    

The ingredients are blended and ground together in a sand mill toproduce particles essentially all under 5 microns in size.

EXAMPLE 20

    ______________________________________                                        Solution                                                                      ______________________________________                                        5-amino-N--[(4-methoxy-6-methyl-1,3,5-triazin-                                2-yl)aminocarbonyl]-2-methylbenzene-                                          sulfonamide                  5%                                               water                       95%                                               ______________________________________                                    

The salt is added directly to the water with stirring to produce thesolution, which may then be packaged for use.

EXAMPLE 21

    ______________________________________                                        Low Strength Granule                                                          ______________________________________                                        2-Methyl-5-[(methylamino)carbonylamino]-N--[(4-                               methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzene-                         sulfonamide                   0.1%                                            attapulgite granules         99.9%                                            (U.S.S. 20-40 mesh)                                                           ______________________________________                                    

The active ingredient is dissolved in a solvent and the solution issprayed upon dedusted granules in a double-cone blender. After sprayingof the solution has been completed, the material is warmed to evaporatethe solvent. The material is allowed to cool and then packaged.

EXAMPLE 22

    ______________________________________                                        Granule                                                                       ______________________________________                                        2-amino-N--[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-                       benzenesulfonamide           80%                                              wetting agent                 1%                                              crude ligninsulfonate salt (containing                                                                     10%                                              5-20% of the natural sugars)                                                  attapulgite clay              9%                                              ______________________________________                                    

The ingredients are blended and milled to pass through a 100 meshscreen. This material is then added to a fluid bed granulator, the airflow is adjusted to gently fluidize the material, and a fine spray ofwater is sprayed onto the fluidized material. The fluidization andspraying are continued until granules of the desired size range aremade. The spraying is stopped, but fluidization is continued, optionallywith heat, until the water content is reduced to the desired level,generally less than 1%. The material is then discharged, screened to thedesired size range, generally 14-100 mesh (1410-149 microns), andpackaged for use.

EXAMPLE 23

    ______________________________________                                        High Strength Concentrate                                                     ______________________________________                                        2-amino-N--[(4-methoxy-6-methylpyrimidin-2-yl)amino-                          carbonyl]benzenesulfonamide  99%                                              silica aerogel              0.5%                                              synthetic amorphous silica  0.5%                                              ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce amaterial essentially all passing a U.S.S. No. 50 screen (0.3 mmopening). The concentrate may be formulated further if necessary.

EXAMPLE 24

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        2-Methyl-5-[(methylamino)carbonylamino]-N--[(4,6-                             dimethoxypyrimidin-2-yl)aminocarbonyl]-                                       benzenesulfonamide          90%                                               dioctyl sodium sulfosuccinate                                                                            0.1%                                               synthetic fine silica      9.9%                                               ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produceparticles essentially all below 100 microns. The material is siftedthrough a U.S.S. No. 50 screen and then packaged.

EXAMPLE 25

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        2-Methyl-5-[(methylamino)carbonylamino]-N--[(4-                               methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzene-                         sulfonamide                  40%                                              sodium ligninsulfonate       20%                                              montmorillonite clay         40%                                              ______________________________________                                    

The ingredients are thoroughly blended, coarsely hammer-milled and thenair-milled to produce particles essentially all below 10 microns insize. The material is reblended and then packaged.

EXAMPLE 26

    ______________________________________                                        Oil Suspension                                                                ______________________________________                                        2-Methyl-5-[(methylamino)carbonylamino]-N--[(4,6-                             dimethoxypyrimidin-2-yl)aminocarbonyl]-                                       benzenesulfonamide         35%                                                blend of polyalcohol carboxylic                                                                           6%                                                esters and oil soluble petroleum                                              sulfonates                                                                    xylene                     59%                                                ______________________________________                                    

The ingredients are combined and ground together in a sand mill toproduce particles essentially all below 5 microns. The product can beused directly, extended with oils, or emulsified in water.

EXAMPLE 27

    ______________________________________                                        Dust                                                                          ______________________________________                                        5-amino-N--[(4,6-dimethoxy-1,3,5-triazin-2-yl)amino-                          carbonyl]-2-methylbenzenesulfonamide                                                                     10%                                                attapulgite                10%                                                Pyrophyllite               80%                                                ______________________________________                                    

The active ingredient is blended with attapulgite and then passedthrough a hammer-mill to produce particles substantially all below 200microns. The ground concentrate is then blended with powderedpyrophyllite until homogeneous.

UTILITY

The compounds of Formula I are useful as herbicides. They may be appliedeither pre- or post-emergence for the control of undesired vegetation.By properly selecting rate and time of application, compounds of thisinvention may be used to modify plant growth beneficially.

The precise amount of the compound of Formula I to be used in any givensituation will vary according to the particular end result desired, theuse involved, the weeds to be controlled, the soil type, the formulationand mode of application, weather conditions, etc. Since so manyvariables play a role, it is not possible to state a rate of applicationsuitable for all situations. Broadly speaking, the compounds of thisinvention are used at levels of about 0.1 to 20 kg/ha with a preferredrange of 0.2 to 10 kg/ha. The lower rates of the range will generally beselected for lighter soils, for plant growth modification, weed controlin crops or in situations in which maximum persistence is not necessary.

The compounds of Formula I may be combined with other herbicides and areparticularly useful in combination with3-(3,4-dichlorophenyl)-1,1-dimethylurea, the triazines such as2,4-bis(isopropylamino)-6-(methylthio)-s-triazine, the uracils such as5-bromo-3-sec-butyl-6-methyluracil, N-(phosphonomethyl)glycine,3-cyclohexyl-1-methyl-6-dimethylamino-s-triazine-2,4-(1H,3H)-dione,N,N-dimethyl-2,2-diphenylacetamide, 2,4-dichlorophenoxyacetic acid (andclosely related compounds),4-amino-6-tert-butyl-3-(methylthio-1,2,4-triazin-5(4H)-one (Lexone®),3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea (Lorox®),1,1'-dimethyl-4,4'-bipyridinium ion and monosodium methanearsonate.

The activity of these compounds was discovered in greenhouse tests. Thetests are described and the data resulting from them are shown below. Itis easily seen from the data that the compounds have utility asherbicides and/or plant growth regulants.

TEST PROCEDURES Test A

Seeds of crabgrass (Digitaria sp.), barnyardgrass (Echinochloacrusgalli), wild oats (Avena fatua), Cassia tora, morningglory (Ipomoeasp.), cocklebur (Xanthium sp.), sorghum, corn, soybean, rice, wheat andnutsedge tubers were planted in a growth medium and treated preemergencewith the chemicals dissolved in a nonphytotoxic solvent. At the sametime, cotton having five leaves (including cotyledonary ones), bushbeans with the third trifoliolate leaf expanding, crabgrass with twoleaves, barnyardgrass with two leaves, wild oats with one leaf, cassiawith three leaves (including cotyledonary ones), morningglory with fourleaves (including the cotyledonary ones), cocklebur with four leaves(including the cotyledonary ones), sorghum with three leaves, corn withthree leaves, soybean with two cotyledonary leaves, rice with twoleaves, wheat with one leaf, and nutsedge with three-five leaves weresprayed. Treated plants and controls were maintained in a greenhouse for16 days, then all species were compared to controls and visually ratedfor response to treatment.

Ratings for compounds tested by this procedure are recorded in TableXIV.

O=no effect

& or 10=maximum effect

C=chlorosis or necrosis

E=emergence inhibition

G=growth retardation

H=formative effects

S=albinism

U=unusual pigmentation

6Y=abscised buds or flowers

W=wilt

X=axillary stimulation

It will be seen that the compounds of Formula I possess excellentherbicidal properties.

    TABLE XIV      POST-EMERGENCE  Rate   Sor-  Soy-  Wild  Barnyard- Crab- Morning- Cock-      Nut-  kg/ha Bush Bean Cotton ghum Corn bean Wheat Oats Rice grass grass     glory lebur Cassia sedge      ##STR171##      2.0 5S,7G,6Y 3C,3H,6G 7U,9G 10C 3C,7H 9C 9C 8C 10C 9C 2C,5H 3C,8G 3C 3G      ##STR172##      2.00.4 3C,9G,6Y6C,9G 3C,5G2C,5G 2C,8G1C,8G 2U,8G 9C 4C,9G9C 3C,7G2C,6G     3C,8G1C,6G 5C,9G4C,8G 9H7H 7G1C 3C,9G2C,9G 3C,9G2C,9G 8C3C,6G 2C,7G1C,6G      ##STR173##      2.00.4 3C,7G,6Y3C,7G,6Y 2C3G 1C,7G1C,8G 9H3U,8G 3C,8G2C,7G,5X 2C,7G1C,6G      2C,8H7G 3C,8G2C,8G 3C1C 3G 2C,7G1C,5G 2C,6H1C,2H 4C2C 5G0      ##STR174##      2.00.4 3S,8G,6Y3S,7G,6Y 3C,7G3C,6G 7U,9G7U,8G 9C9C 3C,8G3C,7G 8C9C 9C9C 8     C10C 10C10C 9C6C,9G 3C,7G2C,6G 5C,8G1C,8G 5C2C 3G3G      ##STR175##      2.00.4 3C,5G,6Y2C,6G,6Y 2C1C 4G4H 5G8H 2C,7G1C,3H 2G2G 2G0 5G4G 1C0 01C 3     C1C,3H 2C,6H2C,7H 3C1C 00       PRE-EMERGENCE  Rate      Wild         kg/ha Sorghum Corn Soybean Wheat     Oats Rice Barnyardgrass Crabgrass Morningglory Cocklebur Cassia Nutsedge      ##STR176##      2.0 9G 9G 7H 9G 2C,8G 10E 2C,9H 2C,8G 8G 8G 8G 10E      ##STR177##      2.00.4 9G1C,9G 10E9G 9H9H 9H9G 8G8G 10E9H 9G9G 7G4G 9C9G  9G9G 9G8G     10E10E      ##STR178##      2.00.4 1C,9G1C,9G 1C,9G2C,9G 8H7H 9G9G 8G1C,7G 10E9H 2C,8G2C,6G 5G2G     9G9G 9G9G 6G5G 9G3G      ##STR179##      2.00.4 1C,9G1C,9G 10E9G 2H,9G5H 1C,9G9G 2C,9G9G  10E10E 9H9H 9C9H 8G8G     9G2H,7G 2C,5G2C,5G 10E9G      ##STR180##      2.00.4 2C8G 1C1C,8G 1C4U 9G9G 8G8G 10E9G 2C,8G1C,6G 5G4G 9G9G 10E4G     2C,8G7G 7G2G       POST-EMERGENCE     Morning- Cock-  Nut- Crab- Barnyard- Wild   Soy-     Sor-  kg/ha Bush Bean Cotton glory lebur Cassia sedge grass grass Oats     Wheat Corn bean Rice ghum      ##STR181##      0.4 2S,7G,6Y 2S,2H,7G 10C 3H,8G 2C,7G 1C,6G 3C,8G 10C 9C 6C,8H 5U,9G     5C,9G 10C 5C,9G      ##STR182##      0.4 2C,2H,5G 2C,2H,7G 1C 1C,5G 3G 4G 9C 10C 5G 5G 8H 0 9C 8H      ##STR183##      0.4 7C,9G,6Y 6C,9G 9C 6C,9G 4C,8G 2C,8G 9C 9C 9C 7C,9G 10C 6C,9G 6C,9G     9C      ##STR184##      0.4 8C,9G,6Y 6C,9G 9C 9C 6C,9G 2C,8G 5C,8G 9C 9C 4C,9G 5U,9C 5C,9G     6C,9G 9C      ##STR185##      0.4 5C,8G,6Y 6C,9G 9C 6C,9G 3C,3H 1C,9G 10C 9C 9C 9C 10C 6C,9G 5C,9G 9C      ##STR186##      0.05 9C 4C,9G 0 3C,9G 1C,3G 1C,5G 3C,8G 3C,9H 6C,9G 5C,9G 5C,9G 9C 9C     4C,9H      ##STR187##      .05 3C,8G,6Y 2C,4G 1C,4G 0 0 1C 1C 3C,7H 1C,4G 1C,5G 2C,7H 2C,7G,5X     2C,9G 2C,9H      ##STR188##      0.4 9C 6C,9G 10C 9C -- 3C,8G 10C 10C 10C 9C 9C 9C 9C 9C      ##STR189##      0.05 3C,8G,6Y 3C,4H 3C,7H 4C,9G 1C 0 1C 1C,3H 1C,3G 1C,2G 0 2C,2H,7G     1C,5G 2C,9H      ##STR190##      .051 00 00 00 00 00 00 00 00 00 00 00 00 0 0 00      ##STR191##      .05 2A,6F 0 3G 0 0 0 2G 2H 0 0 0 0 0 0      ##STR192##      .05 0 0 0 0 0 0 2G 2C,8H 2C 1C 1C,2G 0 8G 2C,8H       PRE-EMERGENCE         Wild       kg/ha Morningglory Cocklebur Cassia     Nutsedge Crabgrass Barnyardgrass Oats Wheat Corn Soybean Rice Sorghum      ##STR193##      0.4 9G 10E 9G 10E 9G 9H 9H 9H 10E 9H 10E 9H      ##STR194##      0.4 9G 8G 8G 10E 7G 9H 7G 7G 9G 8H 10E 9H      ##STR195##      0.4 9G 9H 8G 8G 3C,9G 6C,9H 5C,9H 4C,9G 2C,9G 8H 10E 6C,9G      ##STR196##      0.4 9G9H 5C,9G 10E 6C,9G 7C,9H 6C,9G 9H 10H 9H 10E 6C,9H      ##STR197##      0.4 9G 9H 8G 4G 5G 4C,9H 2C,7G 1C,9G 1C,8G 8H 10E 3C,9H      ##STR198##      0.05 6G9H 8G 2C,7G 2C 3C,9H 3C,9G 9G 1C,9G 2C,5H 9H 5C,9H      ##STR199##      .05 3C 0 1C 0 0 2C 1C,5G 4G 1C,6G 2C,3H 2C,5G 2C,9G      ##STR200##      0.4 9G 9H 2C,9G 10E 6C,9G 9C 9C 1C,9G 1C,9C 9H 10E 5C,9H      ##STR201##      0.05 1C,5H9H 2C 1C,8G 0 1C,7G 1C,8G 1C,9G 1C,7G 2C 2C,8H 2C,9H      ##STR202##      .051 02G 06G 03G 00 00 00 00 00 00 00 00 00      ##STR203##      .05 0 0 0 0 0 0 0 0 0 0 0 0      ##STR204##      .05 0 0 0 0 0 0 0 0 0 0 0 2C     ##STR205##     ##STR206##     ##STR207##

The above compounds were tested at a low rate and were found to beinactive; it is thought that testing at higher rates would result inherbicidal activity being demonstrated.

Test B

In test B, plastic pots filled with Fallsington sandy loam were plantedto soybeans, cotton, alfalfa, corn, rice, wheat, sorghum, velvetleaf(Abutilon theophrasti), sesbania (Sesbania exaltata), Cassia (Cassiatora), morningglory (Ipomoea spp.), jimsonweed (Datura stramonium),cocklebur (Xanthium pennsylvanicum), crabgrass (Digitaria spp.),nutsedge (Cyperus rotundus), barnyardgrass (Echinochloa crusgalli),giant foxtail (Setaria faberii) and wild oats (Avena fatua). Eighteendays after planting, the young plants and the soil around them weresprayed overall with the test chemical dissolved in a nonphytotoxicsolvent. Fourteen day after treatment, all species were compared tountreated controls and visually rated for response to treatment. Theratings are again based on numerical scale extending from 0=no injury,to 10=complete kill. The ratings for the compound tested by thisprocedure are presented in Table XV.

                  TABLE XV                                                        ______________________________________                                         ##STR208##                                                                   Rate kg/ha       .25         .063                                             ______________________________________                                        Soybeans         5G,3H       3G                                               Velvetleaf       3G,3H       0                                                Sesbania                     0                                                Cassia                       0                                                Cotton           0                                                            Morningglory     0           0                                                Alfalfa          10G,7C      5G                                               Jimsonweed       8G,3C       4G                                               Cocklebur        7G          0                                                Corn             10G,7C      10G,4C                                           Crabgrass        10G,6C      7G                                               Rice             10G,4C      8G                                               Nutsedge         0           0                                                Barnyardgrass    7C,10G      8G,2C                                            Wheat            10G,2C      10G                                              Giant Foxtail    10G,3C      8G                                               Wild Oats        10G,4C      7G                                               Sorghum          10G,4C      2C,10G                                           ______________________________________                                         ##STR209##                                                                   Rate kg/ha       .25         .063                                             ______________________________________                                        Soybeans         10G,5H      8G,5H                                            Velvetleaf       3H          0                                                Sesbania                     0                                                Cassia           3G          0                                                Cotton           5G,5H       2H                                               Morningglory     6G          0                                                Alfalfa          7C,10G      5G                                               Jimsonweed       10G,7C      2H                                               Cocklebur        5G          0                                                Corn             10G,7C      9G,3C                                            Crabgrass        8G,3C       3G                                               Rice             10G,4C      8G,3C                                            Nutsedge         0           0                                                Barnyardgrass    4C,10G      10G,3C                                           Wheat            10G,3C      10G                                              Giant Foxtail    10G,3C      8G                                               Wild Oats        10G,4C      10G                                              Sorghum          8G,3C       10G                                              ______________________________________                                         ##STR210##                                                                   Rate kg/ha       .25         .063                                             ______________________________________                                        Soybeans         10G,5H      8G,5H                                            Velvetleaf       5G,3H       0                                                Sesbania         8G          3G                                               Cassia           5G          3G                                               Cotton           5G,2H       0                                                Morningglory     7G,3H       3G,2H                                            Alfalfa          10G,5H      10G,3H                                           Jimsonweed       10G,5C      7G,3H                                            Cocklebur        8G,3H       2G                                               Corn             7G,2U       8G                                               Crabgrass        0           0                                                Rice             6G          5G                                               Nutsedge         0           0                                                Barnyardgrass    3G          0                                                Wheat            7G          3G                                               Giant Foxtail    0           0                                                Wild Oats        5G          0                                                Sorghum          10G,3H      2G                                               ______________________________________                                         ##STR211##                                                                   m.p. 210-215°                                                          Rate kg/ha       0.06        0.25                                             ______________________________________                                        Soybeans         9G,3H       10G,3C                                           Velvetleaf       10C         --                                               Sesbania         8G,4C       10G,7C                                           Cassia           8G,2C       10G,5C                                           Cotton           10G,6C      8G,5C                                            Morningglory     10G,2C      10G,6C                                           Alfalfa          10G,6C      10G,9C                                           Jimsonweed       10G,8C      10G,6C                                           Cocklebur        5G          7G,3H                                            Corn             9G          9G,2C                                            Crabgrass        3G          10G,5H                                           Rice             10G,4C      10G,4C                                           Nutsedge         5G          7G                                               Barnyardgrass    10G,3H      10G,3C                                           Wheat            9G          10G                                              Giant Foxtail    7G          10G,5C                                           Wild Oats        8G,3H       10G,3H                                           Sorghum          10G,3C      10G,3C                                           ______________________________________                                         ##STR212##                                                                   m.p. 204-213°                                                          Rate kg/ha             .03                                                    ______________________________________                                        Soybeans               5G,4H                                                  Velvetleaf             3G                                                     Sesbania               5G                                                     Cassia                 4G                                                     Cotton                 2G,1C                                                  Morningglory           8G,4C                                                  Alfalfa                6G,2C                                                  Jimsonweed             3G                                                     Cocklebur              0                                                      Corn                   7G,3U                                                  Crabgrass              2G                                                     Rice                   8G,3C                                                  Nutsedge               0                                                      Barnyardgrass          9C                                                     Wheat                  5G                                                     Giant Foxtail          5G                                                     Wild Oats              6G                                                     Sorghum                8G,2U                                                  ______________________________________                                    

Test C

Two plastic bulb pans were filled with fertilized and limed Fallsingtonsilt loam soil. One pan was planted with corn, sorghum, Kentuckybluegrass and several grassy weeds. The other pan was planted withcotton, soybeans, purple nutsedge (Cyperus rotundus), and severalbroadleaf weeds. The following grassy and broadleaf weeds were planted:crabgrass (Digitaria sanguinalis), barnyardgrass (Echinochloacrusgalli), wild oats (Avena fatua), johnsongrass (Sorghum halepense),dallisgrass (Paspalum dilatatum), giant foxtail (Setaria faberii),cheatgrass (Bromus secalinus), mustard (Brassica arvensis), cocklebur(Xanthium pennsylvanicum), pigweed (Amaranthus retroflexus),morningglory (Ipomoea hederacea), cassia (Cassia tora), teaweed (Sidaspinosa), velvetleaf (Abutilon theophrasti), and jimsonweed (Daturastramonium). A 12.5 cm diameter plastic pot was also filled withprepared soil and planted with rice and wheat. Another 12.5 cm pot wasplanted with sugarbeets. The above four containers were treatedpre-emergence with several test compounds within the scope of theinvention.

Twenty-eight days after treatment, the plants were evaluated andvisually rated for response to the chemical treatments utilizing therating system described previously for Test A. The data are summarizedin Table XVI.

                  TABLE XVI                                                       ______________________________________                                         ##STR213##                                                                          Rate kg/ha      .25                                                    ______________________________________                                               Crabgrass       0                                                             Barnyardgrass   0                                                             Sorghum         0                                                             Wild Oats       0                                                             Johnsongrass    0                                                             Dallisgrass     0                                                             Giant Foxtail   0                                                             Ky. bluegrass   0                                                             Cheatgrass      0                                                             Corn            0                                                             Mustard         8G                                                            Cocklebur       10C                                                           Pigweed         8G                                                            Nutsedge        0                                                             Morningglory    0                                                             Cassia          0                                                             Teaweed         0                                                             Velvetleaf      0                                                             Jimsonweed      0                                                             Soybean         0                                                             Rice            0                                                             Wheat           0                                                             Sugarbeats      0                                                      ______________________________________                                         ##STR214##                                                                   Rate kg/ha        .25         .063                                            ______________________________________                                        Crabgrass         8G,8H       5G                                              Barnyardgrass     7G,3H       3G                                              Sorghum           8G,5H       3G                                              Wild Oats         4G          0                                               Johnsongrass      3H,5G       0                                               Dallisgrass       10C         0                                               Giant Foxtail     5G,3H       3G,3H                                           Ky. bluegrass     5G          0                                               Cheatgrass        8G,8C       3G                                              Corn              6G,3H       3G                                              Mustard           3G          0                                               Cocklebur         0           0                                               Pigweed                       0                                               Nutsedge          10E         0                                               Morningglory      2G          0                                               Cassia            0                                                           Teaweed                                                                       Velvetleaf        0                                                           Jimsonweed        0                                                           Soybean           0           0                                               Rice              8G,9G       5G                                              Wheat             6G          0                                               Sugarbeats        3G          0                                               ______________________________________                                         ##STR215##                                                                          Rate kg/ha      .25                                                    ______________________________________                                               Crabgrass       0                                                             Barnyardgrass   0                                                             Sorghum         2G                                                            Wild Oats       0                                                             Johnsongrass    0                                                             Dallisgrass     0                                                             Giant Foxtail   3H                                                            Ky. bluegrass   2H                                                            Cheatgrass      2H                                                            Corn            3G                                                            Mustard         0                                                             Cocklebur       0                                                             Pigweed         0                                                             Nutsedge        0                                                             Morningglory    0                                                             Cassia          0                                                             Teaweed                                                                       Velvetleaf      0                                                             Jimsonweed      0                                                             Soybean         0                                                             Rice            0                                                             Wheat           0                                                             Sugarbeats      0                                                      ______________________________________                                        PRE-EMERGENCE ON FALLSINGTON SILT LOAM                                         ##STR216##                                                                   m.p. 210-215°                                                          Rate kg/ha        0.06        0.25                                            ______________________________________                                        Crabgrass         0           5G                                              Barnyardgrass     5G          8G,5H                                           Sorghum           6G,5H       6G,3H                                           Wild Oats         3G          3G                                              Johnsongrass      7G,5H       9G,5H                                           Dallisgrass       4G          6G                                              Giant foxtail     3G          7G,5H                                           Ky. bluegrass     6G          9G,9C                                           Cheatgrass        4G          9G,8C                                           Sugarbeets        6G          9G,9C                                           Corn              3G          9G,9H                                           Mustard           9G,9C       10C                                             Cocklebur         0           5G                                              Pigweed           10E         10E                                             Nutsedge          6G          7G                                              Cotton            0           7G                                              Morningglory      5G          7G                                              Cassia            5G          8G                                              Teaweed           0           3C                                              Velvetleaf        3G          7G                                              Jimsonweed        5G          7G                                              Soybean           4G          6G,3H                                           Rice              6H          9H                                              Wheat             3G          5G                                              ______________________________________                                        PRE-EMERGENCE ON FALLSINGTON SILT LOAM                                         ##STR217##                                                                   m.p. 204-213°                                                          Rate kg/ha        0.03        0.12                                            ______________________________________                                        Crabgrass         0           0                                               Barnyardgrass     3G          5G                                              Sorghum           0           3G                                              Wild Oats         0           0                                               Johnsongrass      0           3G                                              Dallisgrass       0           0                                               Giant foxtail     0           0                                               Ky. bluegrass     0           5G                                              Cheatgrass        0           3G                                              Sugarbeets        0           3G                                              Corn              0           0                                               Mustard           0           8G,3C                                           Cocklebur         0           0                                               Pigweed           3G          8G,5C                                           Nutsedge          0           0                                               Cotton            0           3G                                              Morningglory      0           2G                                              Cassia            0           2G                                              Teaweed           0           0                                               Velvetleaf        0           0                                               Jimsonweed        0           0                                               Soybean           0           0                                               Rice              3G          7G,5H                                           Wheat             0           4G                                              ______________________________________                                        PRE-EMERGENCE ON FALLSINGTON SILT LOAM                                         ##STR218##                                                                   m.p. 132-135°                                                          Rate kg/ha        0.03        0.12                                            ______________________________________                                        Crabgrass         0           0                                               Barnyardgrass     0           0                                               Sorghum           0           3G                                              Wild Oats         0           0                                               Johnsongrass      0           0                                               Dallisgrass       0           0                                               Giant foxtail     0           0                                               Ky. bluegrass     0           4G                                              Cheatgrass        0           0                                               Sugarbeets        0           0                                               Corn              0           0                                               Mustard           0           0                                               Cocklebur         0           0                                               Pigweed           0           6G                                              Nutsedge          0           0                                               Cotton            0           0                                               Morningglory      0           0                                               Cassia            0           0                                               Teaweed           0           0                                               Velvetleaf        0           0                                               Jimsonweed        0           0                                               Soybean           0           0                                               Rice              0           0                                               Wheat             0           0                                               ______________________________________                                        PRE-EMERGENCE ON FALLSINGTON SILT LOAM                                         ##STR219##                                                                   m.p. 205-212°                                                          Rate kg/ha        0.03        0.12                                            ______________________________________                                        Crabgrass         0           0                                               Barnyardgrass     0           3G                                              Sorghum           0           3G                                              Wild Oats         0           0                                               Johnsongrass      0           3G                                              Dallisgrass       0           0                                               Giant foxtail     0           0                                               Ky. bluegrass     3G          3G                                              Cheatgrass        0           0                                               Sugarbeets        0           0                                               Corn              0           0                                               Mustard           0           6G                                              Cocklebur         0           0                                               Pigweed           0           4G                                              Nutsedge          0           0                                               Cotton            0           0                                               Morningglory      0           0                                               Cassia            0           0                                               Teaweed           0           0                                               Velvetleaf        0           3G                                              Jimsonweed        0           0                                               Soybean           0           0                                               Rice              3G          6G                                              Wheat             0           0                                               ______________________________________                                        PRE-EMERGENCE ON FALLSINGTON SILT LOAM                                         ##STR220##                                                                   m.p. 216-218°                                                          Rate kg/ha        0.03        0.12                                            ______________________________________                                        Crabgrass         0           0                                               Barnyardgrass     0           2G                                              Sorghum           0           3G                                              Wild Oats         0           0                                               Johnsongrass      0           3G                                              Dallisgrass       --          --                                              Giant foxtail     0           0                                               Ky. bluegrass     4G          3G                                              Cheatgrass        --          --                                              Sugarbeets        0           0                                               Corn              0           0                                               Mustard           0           5G,3H                                           Cocklebur         0           0                                               Pigweed           5G          7G                                              Nutsedge          0           0                                               Cotton            0           0                                               Morningglory      0           0                                               Cassia            --          0                                               Teaweed           0           0                                               Velvetleaf        0           0                                               Jimsonweed        0           0                                               Soybean           0           2G                                              Rice              0           3G                                              Wheat             0           0                                               ______________________________________                                        PRE-EMERGENCE ON FALLSINGTON SILT LOAM                                         ##STR221##                                                                   m.p. 104-106°                                                                 Rate kg/ha      0.03                                                   ______________________________________                                               Crabgrass       0                                                             Barnyardgrass   0                                                             Sorghum         0                                                             Wild Oats       0                                                             Johnsongrass    0                                                             Dallisgrass     0                                                             Giant foxtail   0                                                             Ky. bluegrass   0                                                             Cheatgrass      0                                                             Sugarbeets      0                                                             Corn            0                                                             Mustard         3G                                                            Cocklebur       0                                                             Pigweed         0                                                             Nutsedge        0                                                             Cotton          0                                                             Morningglory    0                                                             Cassia          0                                                             Teaweed         0                                                             Velvetleaf      0                                                             Jimsonweed      0                                                             Soybean         0                                                             Rice            0                                                             Wheat           0                                                      ______________________________________                                    

Test D

Compounds were applied to both black valentine ("pole" type) andtendercrop beans ("bush" type). The treatment was applied in a suitablenonphytotoxic solvent when the black valentine beans had the firsttrifoliolate leaf and the developing tendercrop beans were in the earlyflower bud stage. Treated plants and controls were maintained in agreenhouse and response ratings taken 1 and 4 weeks after treatment. Podyields were taken between 3 and 4 weeks after treatment. Yield resultsare recorded as a percentage of untreated controls. Ratings forcompounds tested by this procedure are recorded in Table XVII.

                  TABLE XVII                                                      ______________________________________                                        POLE BEAN      BUSH BEAN                                                             1       4       1     4            Fruit                               Kg/Ha  Week    Weeks   Week  Weeks No. Fruit                                                                            Weight                              ______________________________________                                         ##STR222##                                                                   .031   3C      6C      3C    3C    0      0                                          5G      7G      3G    3G                                               .125   5C      8C      5C    7C    0      0                                          6G      7G      4G    4G                                               .5     4H      9C      5H    9C    0      0                                          7C      9G      7C    8G                                                      9G              8G                                                     ______________________________________                                         ##STR223##                                                                   .125   3C      4C      4C    3G    2       0                                         4G      5G      3G    3C                                                                            2H                                               .5     6C      8C      6C    7C    0      0                                          7G      8G      5G    7G                                               2.0    7C      10C     7C    6C    0      0                                          8G              7G    4H                                                                            6G                                               ______________________________________                                    

Test E

Purple nutsedge (Cyperus rotundus) tubers were planted about 2 cm deepin Fallsington silt loam soil contained in 10 cm diameter plastic pots.Five tubers were planted in each pot. Compounds of this invention weredissolved in a non-phytotoxic diluent and sprayed at 560 l/ha in fourmethods of application: soil surface, tuber/soil, soil incorporated andpost-emergence. The soil surface spray consisted of spraying thecompound on the surface of the firmed covering soil. The tuber/soilspray consisted of spraying the compound on exposed tubers andsubtending soil before adding the untreated covering soil. Soilincorporated treatment consisted in mixing the compound with thecovering soil before using it to cover the tubers. The post-emergencetreatment was sprayed on nutsedge foliage and the surrounding soilsurface when nutsedge had emerged and grown to a height of about 12 cm.Pots receiving the post-emergence treatments were placed directly in thegreenhouse. Pots receiving the other treatments were misted with about0.3 cm water before being transferred to the greenhouse. Responseratings assessed after four weeks are recorded in Table XVIII based onthe same rating system as described in procedure A.

    ______________________________________                                        Perennial Grass Screen                                                        Nutsedge Control                                                               ##STR224##                                                                   Response Rating (After 4 Weeks)                                               Rate    Preemerg.  Tuber     Soil                                             kg/ha   Soil Surface                                                                             Spray     Incorp.                                                                             Postemerg.                                 ______________________________________                                        .125    0          0         0     0                                          .5      8E,9G      8E,8G     10E   7C                                         ______________________________________                                    

                  TABLE XVIII                                                     ______________________________________                                        PLANT RESPONSE 4 WEEKS AFTER TREATMENT                                         ##STR225##                                                                           Pre     Pre          Pre                                              Rate,   surface tuber + soil soil inc.                                                                            Post                                      kg/ha   spray   spray        2.5 cm foliar spray                              ______________________________________                                        2.0     3E      3C           3C     4W                                                8C      7G           8G     3G                                        0.5     0       2G           2G     0                                         ______________________________________                                    

What is claimed is:
 1. A compound selected from ##STR226## wherein R₁ isH, Cl, Br, F, alkyl of 1-4 carbon atoms, OCH₃, NO₂ or R₁₁ S(O)_(m) ;R₂is --NCO, --NHCOOR₃, --NHCOSR₃, --NHCOR₃, --NHCONR₄ R₅ or --NR₆ R₇ ; R₃is alkyl of 1-4 carbon atoms; R₄ is H or CH₃ ; R₅ is H, alkyl of 1-4carbon atoms or methoxy; R₆ is H or alkyl of 1-3 carbon atoms; R₇ is Hor alkyl of 1-3 carbon atoms; or R₆ and R₇ taken together are

    --(CH.sub.2).sub.n --or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --;

n is 4 or 5; R₁₁ is alkyl of 1-3 carbon atoms; m is 0 or 2; X is methyl,methoxy or ethoxy; Y is methyl or methoxy; and Z is CH;provided that:(a) when R₂ is ortho to the sulfonylureido group, then R₁ must behydrogen and R₂ cannot --NCO; (b) when R₅ is methoxy, R₄ is methyl; (c)when R₂ is --NCO, the compound cannot be a salt.
 2. A compound of claim1 whereinR₂ is --NR₆ R₇, --NCO, --NHCOOCH₃, --NHCOCH₃ or --NHCON(CH₃)₂ ;and R₆ and R₇ are independently hydrogen or alkyl of 1-3 carbon atoms.3. A compound of claim 1 whereinR₁ is alkyl of 2-3 carbon atoms or R₁₁S(O)_(m).
 4. A compound of claims 2 or 3 whereinR₂ is --NR₆ R₇ or --NCO;R₆ and R₇ are independently hydrogen or methyl; and X is methyl ormethoxy.
 5. A compound of claims 2-4 whereinR₁ is hydrogen, chlorine,methyl or methoxy.
 6. The compound of claim1,Methyl[3-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]phenyl]carbamate.7. The compound of claim1,(1-Methylethyl)[3-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]phenyl]carbamate.8. The compound of claim1,3-isocyanato-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide.9. The compound of claim1,3-(3,3-dimethylureido)-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide.10. The compound of claim1,2-amino-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide.11. The compound of claim1,2-amino-N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide.12. The compounds of claim15-amino-N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-methylbenzenesulfonamide.13. The compound of claim1,5-amino-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-methylbenzenesulfonamide.14. The compound of claim1,5-amino-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methylbenzenesulfonamide.15. The compound of claim1,2-Methyl-5-[(methylamino)carbonylamino]-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide.16. The compound of claim1,2-Methyl-5-[(methylamino)carbonylamino]-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide.17. The compound of claim1,2-amino-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide.18. The compound of claim1,N-[2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]phenyl]acetamide.19. The compound of claim1,N-[2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]phenyl]acetamide.20. The compounds of claim1,N-[2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]phenyl]acetamide.21. A composition for the control of undesirable vegetation consistingessentially of a compound of claim 1 and at least one of (a) asurface-active agent and (b) a solid or liquid diluent.
 22. Acomposition for the control of undesirable vegetation consistingessentially of a compound of claim 2 and at least one of (a) asurface-active agent and (b) a solid or liquid diluent.
 23. Acomposition for the control of undesirable vegetation consistingessentially of a compound of claim 3 and at least one of (a) asurface-active agent and (b) a solid or liquid diluent.
 24. Acomposition for the control of undesirable vegetation consistingessentially of a compound of claim 4 and at least one of (a) asurface-active agent and (b) a solid or liquid diluent.
 25. Acomposition for the control of undesirable vegetation consistingessentially of the compound of claim 5 and at least one of (a) asurface-active agent and (b) a solid or liquid diluent.
 26. Acomposition for the control of undesirable vegetation consistingessentially of the compound of claim 6 and at least one of (a) asurface-active agent and (b) a solid or liquid diluent.
 27. Acomposition for the control of undesirable vegetation consistingessentially of the compound of claim 7 and at least one of (a) asurface-active agent and (b) a solid or liquid diluent.
 28. Acomposition for the control of undesirable vegetation consistingessentially of the compound of claim 8 and at least one of (a) asurface-active agent and (b) a solid or liquid diluent.
 29. A method forthe control of undesirable vegetation comprising applying to the locusof such undesirable vegetation a herbicidally effective amount of acompound of claim
 1. 30. A method for the control of undesirablevegetation comprising applying to the locus of such undesirablevegetation a herbicidally effective amount of a compound of claim
 2. 31.A method for the control of undesirable vegetation comprising applyingto the locus of such undesirable vegetation a herbicidally effectiveamount of a compound of claim
 3. 32. A method for the control ofundesirable vegetation comprising applying to the locus of suchundesirable vegetation a herbicidally effective amount of a compound ofclaim
 4. 33. A method for the control of undesirable vegetationcomprising applying to the locus of such undesirable vegetation aherbicidally effective amount of a compound of claim
 5. 34. A method forthe control of undesirable vegetation comprising applying to the locusof such undesirable vegetation a herbicidally effective amount of thecompound of claim
 6. 35. A method for the control of undesirablevegetation comprising applying to the locus of such undesirablevegetation a herbicidally effective amount of the compound of claim 7.36. A method for the control of undesirable vegetation comprisingapplying to the locus of such undesirable vegetation a herbicidallyeffective amount of the compound of claim
 8. 37. A compound of claim 1where R₁ is H, Cl, Br, F, CH₃, OCH₃ or NO₂.